Not Another CEO Podcast

How do you scale exceptional customer support without losing the human touch?In this episode, David sits down with Ryan Wang, Co-Founder and CEO of Assembled, to explore this very challenge. What started as a simple scheduling tool has evolved into an AI-powered customer support platform trusted by leading companies like DoorDash and Salesforce.Ryan opens up about the realities of scaling a fast-growing company, balancing innovation with culture, leading through learning, and keeping mission and execution at the heart of everything. His insights offer a playbook for founders and leaders aiming to build resilient, adaptable organizations.Takeaways:Understanding the Challenge of Scaling Support: Ryan Wang shares insights into the evolution of Assembled, beginning with a fundamental question: how to scale great customer support without losing efficiency..Wearing Multiple Hats: Ryan emphasizes the importance of diving into different roles within a company. For founders, this means deeply engaging with various functions, learning from their challenges, and understanding what excellence looks like.The Art of Networking: The conversation highlights the importance of connecting with top industry leaders to learn and seek guidance. Founders should prioritize genuine learning over mere networking, making it easy for mentors to share their expertise.Adaptability and Product Evolution: Assembled’s journey reflects the necessity of being adaptable. Ryan discusses the creation of a "new products" team to innovate without disrupting the existing structure, showcasing a strategic approach to product development.Facing Cultural Challenges: The transition to AI tools and methods posed cultural challenges at Assembled. Ryan acknowledges how these changes can strain company culture, advising that clear communication and integrating efforts can prevent breaking the company culture.Mission and Execution: Ryan and David discuss how a strong mission and purpose can act as a modern moat for companiesQuote of the Show:“As CEO, your job is to hold the line, even when it breaks hearts, because someone has to protect the long-term vision." - Ryan WangLinks:LinkedIn: https://www.linkedin.com/in/ryanywang/ Website: https://www.assembled.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 #AssembledChapters:00:00 Intro01:22 Deep Dive into Leadership and Management04:25 Networking with Industry Leaders09:12 Balancing Multiple Roles as CEO15:31 Transition to CEO Role23:33 Evolution of Assembled's Product29:13 Running Through Y Combinator30:28 Demo Days and Team Dynamics32:16 Staying on Top of Rapid Changes35:53 The Concept of Moat in Business40:22 Adapting to AI and Cultural Challenges45:09 Future Vision for Assembled47:42 Personal Background and Influences52:45 Advice for Aspiring Entrepreneurs55:15 Outro

How can founders build companies that scale without burning themselves out in the process?In this episode, Noah Shanok, Founder and former CEO of Stitcher, reflects on his entrepreneurial journey leading one of the earliest podcast platforms, which ultimately sold to SiriusXM for $325 million. He shares candid lessons from the early days of Stitcher, navigating sleepless nights, hiring versatile early employees, and learning from missteps along the way.Noah also discusses how his time at Amazon influenced his approach to structured hiring, why prioritizing personal well-being is critical for long-term effectiveness, and how founders can overcome imposter syndrome. Now working as a coach to entrepreneurs, he brings a unique perspective on balancing growth with sustainability, drawing on both successes and challenges from his own journey.Prioritize Yourself as a Founder: Noah candidly discussed his early days at Stitcher, which were characterized by overworking, sleep deprivation, and unhealthy habits. He advocates for founders to prioritize their well-being to ensure they can think clearly in the short term while remaining effective in the long run.Building the Right Team: Noah emphasized the impact of hiring a versatile team early on. His advice to recruit a "jack of all trades" who can adapt and grow with the company resonates with many startup leaders.Overcoming Imposter Syndrome: Noah addressed the imposter syndrome prevalent among founders. He shared strategies to navigate these feelings by focusing on decision-making confidence and holding oneself accountable.The Importance of Timing and Market Dynamics: Reflecting on Stitcher’s challenges, Noah acknowledged the role of timing and market forces. Factors such as market readiness and timing of product launches are crucial in scaling a business successfully, emphasizing that external shifts can heavily influence a startup’s trajectory regardless of internal effort and execution.Leveraging Strategic Partnerships: Noah’s success in securing high-profile deals started with creating strategic partnerships. By working with seasoned advisors, founders can effectively enter new markets and secure pivotal deals that may hasten growth and establish industry credibility.Quote of the Show:“ I've helped hire hundreds of people at Amazon. If I started another company I would implement a very light version of Amazon's process, and I would do it very, very early." - Noah ShanokLinks:LinkedIn: https://www.linkedin.com/in/noahshanok/ Website: https://startupceo.coach/ 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 #StitcherChapters:00:00 Intro01:42 The Importance of Hiring a Versatile Team Member02:24 Finding the Right Person for the Job07:00 Lessons from Amazon's Hiring Process13:29 Stitcher's Early Business Development Deals21:37 Challenges and Realities of Strategic Partnerships26:53 Coaching Founders: Common Challenges and Solutions32:29 Transformative Changes and New Habits33:13 The Impact of Prioritizing Self-Care37:50 The Power of CEO Support Systems38:24 Dealing with Imposter Syndrome45:24 Lessons from Stitcher: Timing and Market Dynamics48:58 The Drive to Build and Help Others51:50 The Importance of Mentors and Advisors57:25 The Need for a Support System for CEOs59:38 Advice for Founders 1:00:58 Outro

Do you know how essential a support system is for a CEO? In this solo episode of Not Another CEO Podcast, David discusses the often overlooked, yet critical support necessary for CEO success.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 #OctoberCEOPulseChapters:00:00 Intro02:53 The Importance of a CEO Support System03:57 Key Components of a CEO Support System05:10 The Role of Co-Founders and Key Executives07:33 The Value of Executive Assistants and Chiefs of Staff09:24 Leveraging Board Members and Advisors14:38 The Importance of Therapists and Personal Relationships19:16 The Power of CEO Peer Networks21:27 Outro

What can founders learn from an entrepreneur who has built, scaled, and exited multiple companies while reshaping an entire city’s startup ecosystem?In this episode, David Cummings, Founder and CEO of Atlanta Ventures, reflects on his journey building ten companies, including Pardot, which sold to ExactTarget for $95 million, and investing in some of Atlanta’s most successful startups like Calendly and SalesLoft. He shares the guiding principles that shaped his entrepreneurial path, from building a culture-first company to navigating the realities of bootstrapping, scaling, and liquidity events.David also opens up about his role in transforming Atlanta’s tech landscape through Atlanta Tech Village and his ambitious project to redevelop South Downtown into a vibrant startup district. Along the way, he offers candid advice for founders on leadership, resilience, and blending work with life in a sustainable way.Visionary Leadership: Cummings underscores the importance of having a clear and opinionated vision. The strategy of creating a product that provides "the most bang for the buck" without falling into the trap of building every requested feature was crucial to Pardot’s success.Bootstrapping Success: Despite the odds against fundraising in a nascent market, Cummings attributes his company’s success to resilient bootstrapping. This allowed him to maintain control and leverage opportunities like strategic acquisitions without compromising his vision.Cultivating Culture: A major highlight from Cummings' leadership was the deliberate cultivation of a workplace culture that prioritizes being positive, self-starting, and supportive.Balancing Ambitions and Personal Life: As an advocate for the "work-life blend," Cummings emphasizes that while early-stage startups demand an intense commitment, sustaining a balanced life is about integrating passion for work with personal commitments.A Tech Renaissance in Atlanta: Cummings' latest venture involves the redevelopment of a historic part of Atlanta into a vibrant startup district. This ambitious project aims to transform south downtown Atlanta into a living ecosystem for innovation and growth, reinforcing Atlanta’s position as a world-class city with a thriving entrepreneurial community.Quote of the Show:“All the entrepreneur styles are different. But for me personally, I'm that shock absorber style. I recognize that things can be great and things can be bad, and just modulate it for the team." - David CummingsLinks:LinkedIn: https://www.linkedin.com/in/davidcummings/ Website: https://www.atlantaventures.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 #AtlantaVenturesChapters:00:00 Intro01:44 Early Challenges and Successes at Pardot02:24 Building a Strong Company Culture03:02 Product Vision and Customer Focus05:55 Transition from Doer to Leader12:49 Bootstrapping vs. Fundraising20:34 The ExactTarget Acquisition31:08 Reflections on Entrepreneurship and Liquidity36:52 Understanding Startup Valuations38:09 Building a Winning Team at Pardot41:17 Investing in Founders with the Right Attributes43:29 The Atlanta Tech Village Journey51:44 Revitalizing Downtown Atlanta01:00:56 David's Entrepreneurial Beginnings01:06:57 Balancing Entrepreneurship and Family01:10:36 Advice for Aspiring Entrepreneurs01:12:50 Outro

THE FIRST EPISODE OF INVESTORS UNFILTERED!What do venture capitalists really look for in founders, and how can CEOs build strong, lasting relationships with their investors? In this episode, Chip Hazard, Co-Founder and General Partner at Flybridge, offers an inside look at how VCs think about evaluating founders, funding opportunities, and long-term partnerships. He shares the traits that consistently stand out and explains how these factors matter as much as business metrics, especially in the early stages.Chip also unpacks the evolution of fundraising, from vision-driven early rounds to later stages where metrics and revenue quality become critical. He reflects on the dynamics of board relationships, the importance of clear alignment on strategy, and why constructive feedback and ongoing communication are vital to scaling effectively. Takeaways:Ambition is Key: Chip emphasizes the importance of passion and ambition in founders. He's looking for those with domain expertise and unconventional thinking.Alignment on Strategy: For founders, aligning on strategy with investors is crucial. Chip notes that understanding an investor’s vision for the company can prevent conflicts and foster a positive partnership.Ongoing Communication: Chip discusses the importance of consistent communication between founders and investors, particularly in the early stages. Regular check-ins on strategy, challenges, and progress help maintain alignment and support.Insightful Board Interactions: The role of a board is to offer perspective and support strategic decision-making. Chip highlights that effective board meetings should align on strategy and not create unnecessary work for the company.Balancing Metrics and Vision: As companies evolve from pre-seed to later stages, the focus shifts from purely vision and team to include metrics and financial performance.The Value of Constructive Feedback: Constructive, honest feedback is essential. Chip stresses that a good VC relationship involves recognizing challenges, offering guidance, and maintaining trust without dictating to the founder.Quote of the Show:“ Startups win on speed. They don’t have anything else other than the ability to execute fast." - Chip HazardLinks:LinkedIn: https://www.linkedin.com/in/chiphazard/ Website: https://www.flybridge.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 #FlybridgeChapters:00:00 Intro02:11 The Key Traits of Successful Founders04:09 Assessing Founders Beyond the Pitch06:04 Stages of Investment and What VCs Look For15:36 Working with Founders Post-Investment22:08 The Importance of External Perspectives25:52 Challenges in Board Dynamics30:37 Aligning with Venture Capitalists37:55 Geographical Differences in Startups40:13 Reflections and Regrets in Venture Capital43:18 The Passion for Investing45:47 Outro

What does it take to reinvent an entire industry that’s been rooted in tradition for decades? In this episode, Michael Jacobson, CEO of French Florist, shares his journey from corporate consulting to transforming the floral business.Michael explains how he grew a single 3,000-square-foot location into a $9 million operation by modernizing systems, cutting inefficiencies from the supply chain, and infusing emotion into every part of the customer experience. He also reflects on the challenges of scaling in a traditional industry, the decision to franchise, and the importance of mentorship, high standards, and culture in building a business that lasts. Takeaways:Develop a Strong Brand Identity: A major part of Jacobson’s strategy was creating branding that emphasizes emotional connection, redefining flowers as essential expressions of love rather than luxury items. Listen to Your Employees: Before anything else, Jacobson prioritized understanding the needs of the staff already working in the flower shop. Their insights provided critical low-hanging fruit, such as switching outdated and costly phone systems, which paved the way for larger innovations.Direct-to-Source Supply Chain: By eliminating unnecessary intermediaries in the supply chain, French Florist improved both the quality and cost-efficiency of their products. Direct relationships with flower farms allowed the business to offer fresher flowers with longer shelf life at competitive prices.Prioritize Customer Experience: French Florist’s focus on exceeding customer expectations through personalized service has been crucial. They constantly seek ways to enhance customer satisfaction, such as offering unique video card messages to accompany floral deliveries.Strategic Hiring and Internal Culture: Hiring talented individuals who align with the company’s values and culture has been a priority. Jacobson emphasizes unconventional and thoughtful interview processes to ensure new hires share the company’s vision and drive.Quote of the Show:“ If it ain’t broke, don’t fix it is one of my least favorite sayings. If there’s a better way, I want to find it." - Michael JacobsonLinks:LinkedIn: https://www.linkedin.com/in/michaelrichardjacobson/ Website: https://www.frenchflorist.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 #FrenchFloristChapters:00:00 Intro01:38 Transformative Leadership and Infusing Emotion03:22 Building a Culture of Love and Excellence08:25 Hiring for Values and Unconventional Interviews14:51 The Origin Story of French Florist19:19 Initial Challenges and Early Improvements24:36 Revolutionizing the Floral Industry with Technology31:43 Revenue Growth and Optimization33:15 Supply Chain Innovations35:15 Direct Importing from Farms37:36 Challenges in the Floral Industry40:28 Franchising and Expansion48:18 Personal Reflections and Motivation1:01:01 Outro

How can CEOs stay adaptable while leading through pivots, growth, and constant change? In this episode, Scott Voigt, Founder and CEO of Fullstory, shares his journey from a failed first product to creating the leading digital analytics platform used by thousands of companies worldwide. Scott dives into the tough realities of leadership, from making difficult people decisions to evolving as a CEO as the company scales. He opens up about the power of storytelling in fundraising and leadership, the importance of mental well-being, and the lessons he’s learned from being an early builder in Atlanta’s thriving tech ecosystem. Takeaways:The Power of Storytelling: Scott Voigt emphasizes the significance of storytelling in his role as CEO. It's not just about what you say but how you say it. Through effective storytelling, he energizes and aligns his team, creating a shared vision and purpose.Hiring and Building a Strong Team: Voigt discusses the challenges of hiring and the importance of finding the right fit. He stresses the necessity of moving people out quickly if they are not a good fit, even though it can be difficult.Navigating Investor Relations: Scott’s journey of securing funding for Fullstory involved both challenges and triumphs. He shares the importance of being strategic and deliberate in choosing investors and board members.The Journey of Fullstory's Market Fit: Voigt candidly reflects on the evolution of Fullstory's product-market fit. Initially, as the team worked on a different product, they faced numerous rejections. However, the pivot to Fullstory's current offering brought about an immediate and undeniable product-market fit.Overcoming Internal Challenges: Discussing exits, Voigt argues that the company's mission should transcend any individual's role, ensuring continued alignment and progress regardless of internal changes.Quote of the Show:“When your spidey sense tells you something isn’t working with a person, make the change fast. It only gets harder the longer you wait." - Scott VoigtLinks:LinkedIn: https://www.linkedin.com/in/scottmvoigt/ Website: https://www.fullstory.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 #FullstoryChapters:00:00 Intro01:36 The Biggest Impactful Decision at Fullstory03:35 The Challenges and Lessons of Letting People Go08:38 Hiring Philosophy and Interview Techniques18:56 The Importance of Storytelling as a CEO24:54 Fundraising Journey and Product Pivot33:38 Reflecting on the Early Struggles37:14 The Importance of Team Chemistry43:28 Navigating the Atlanta Tech Scene48:20 Biggest Challenges and Lessons Learned51:01 Future Vision for Fullstory57:15 Personal Reflections and Advice01:07:53 Outro

Max Junestrand, Co-founder and CEO of Legora, shares his journey from engineer to entrepreneur, paving a unique path in the legal tech industry. He discusses the challenges of scaling a global AI-driven platform while emphasizing the importance of collaboration and cultural fit in hiring. Max reveals insights from his transformative Y Combinator experience, tackling technical hurdles, and navigating hypergrowth. His ambitious vision aims to reshape legal services, focusing on delivering real value while maintaining a strong company culture.

Ever wondered what to consider when hiring your first key employees beyond the founding team? Or what are the secrets to successful fundraising for startups? In this solo episode of Not Another CEO Podcast, David shares his insights from CEO gatherings, trends he’s noticed in the community, and a recent family trip that emphasizes the importance of origin stories.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 #AugustCEOPulseChapters:00:00 Intro02:55 Hiring Your Founding EA13:08 Fundraising Isn’t Fair18:55 The Importance of Origin Stories23:55 Outro

What does it take to build and scale a company while staying grounded in your values? In this episode, Flint Lane reflects on his journey founding and growing Billtrust and coming out of retirement to start Major League Table Tennis. He shares lessons on resilience, leadership, and the balance between personal integrity and business success. Flint also discusses the challenges of navigating growth, what he has learned about himself along the way, and the importance of staying true to purpose even in difficult times. Takeaways:Scaling Begins with Small Wins: Flint emphasizes the importance of "stacking wins" in business, where each small victory propels you forward. He believes the key to success lies in maintaining momentum and making rapid, intelligent decisions.The Role of Mission and Values: For Flint, defining mission and values within a company is crucial for guiding decision-making processes. These elements serve as the company's moral compass, helping employees make decisions aligned with the organization's goals.Navigating Executive Leadership: Flint shares insights into the dynamics of leadership and succession planning. He describes the challenging process of evolving leadership roles to meet the company's growing demands.Overcoming Cybersecurity Challenges: Flint recounts a severe malware attack that tested the company's resilience. He stresses the importance of investing in robust cybersecurity measures and learning from such incidents to better protect critical business assets.The Power of Transparency: Flint argues for fostering trust and collaboration within the organization. By openly communicating challenges and strategies with his team, Flint was able to cultivate an environment of honesty and collective problem-solving.The Entrepreneurial Lifecycle: Flint illustrates the different stages of a company's growth, each with unique challenges and opportunities. From startup to public company, the journey requires adaptation and learning.Transitioning from Software to Sports: After two decades at Billtrust, Flint embarked on a new venture with Major League Table Tennis, driven by his passion for the sport.Quote of the Show:“Any business is a combination of hundreds of thousands, if not millions of decisions, millions of small, little victories." - Flint LaneLinks:LinkedIn: https://www.linkedin.com/in/flintlane/Website: https://www.mltt.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 #MajorLeagueTableTennisChapters:00:00 Intro01:23 Flint Lane's New Venture: Major League Table Tennis01:56 The Importance of Stacking Wins04:06 Effective Communication and Decision Making06:30 The Role of Transparency in Leadership14:51 Hiring the Right People21:06 The Evolution of Executive Teams27:17 The Importance of a Strong Board31:53 Navigating the Startup Journey33:19 The Decision to Go Public36:34 The Acquisition Process39:06 Cybersecurity Crisis43:54 Transition to Major League Table Tennis49:33 Reflections on Entrepreneurship56:46 Final Thoughts and Advice57:48 Outro