Not Another CEO Podcast

What does it take to transform a struggling startup into a booming enterprise? In this episode of Not Another CEO Podcast, host David Politis sits down with Didi Gurfinkel, Co-Founder and CEO of Datarails. Together, they delve into Didi's decade-long journey of building a successful financial platform from scratch, discussing both the struggles and triumphs of his entrepreneurial path.From his early days at Cisco to co-founding Datarails, Didi shares invaluable lessons on startup pivoting, embracing new technologies, and harnessing AI to revolutionize financial operations.Takeaways: The Power of the Right Team: Didi highlights the importance of having the right co-founders. He credits the success of Datarails largely to the strong foundational team that shared common goals and complementary skills.Embracing the Brutal Truth: Didi emphasizes the need for leaders to be honest about their failures and to learn from them while maintaining a visionary outlook for the future.Importance of Having a Name: Drawing from past experiences, Didi advises startups to choose a product that has a recognisable name and existing budget line.Finding Your Ideal Market Fit: Datarails achieved success by narrowing their focus to finance professionals who love Excel, aligning product benefits with users’ existing skills and preferences.Strategic Use of AI: Datarails seeks to prepare organizations for AI integration, ensuring readiness for technological advancements.Balancing Work and Family: Didi points out that while entrepreneurship is all-consuming, showcasing the possibility of building something significant can offer invaluable lessons for family.Quote of the Show:“If someone ask me, I'm not sure if I have the product market fit, I'm saying, no, you don't have it. If you had it, you know." - Didi GurfinkelLinks:LinkedIn:https://www.linkedin.com/in/didigurfinkel/ Website: https://www.datarails.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 #DatarailsChapters:00:00 Intro01:21 Co-Founders Matter Most02:28 Finding the Right Partners05:47 Evolving Founder Roles07:28 Five Tough Early Years09:28 Building Tech Without Sales13:08 Staying Motivated to Pivot18:05 The Breakthrough Pivot20:52 Why FP&A and Mid-Market24:40 Scrappy Early Go-To-Market26:38 LinkedIn Phone Number Hack28:17 Knowing Product Market Fit30:43 Removing Buying Friction32:47 Zero to One Million ARR35:26 AI and Finance OS Vision41:38 Three Year Company Outlook43:06 Founder Origin Story46:25 Israel Startup Mindset47:50 No Work Life Balance51:02 Outro

What sets apart the founders who persevere through immense challenges and come out stronger on the other side? In this episode, David sits down with Shaun Abrahamson, Co-Founder & Managing Partner at Third Sphere. Shaun shares his unique insights into the high-stakes world of venture investing, particularly in climate tech and hardware, reflecting on the kinds of founders he backs and the unforeseen hurdles they've had to overcome.Shaun delves into his philosophy on investing in early-stage companies, emphasizing the importance of resilience and adaptability in founders. He also discusses the intricacies of climate tech investment and the lessons he's learned from over two decades in the field.  Takeaways:The Importance of "Burned Bridges": Shaun explains that he looks for founders who feel they have no option but to succeed, drawing a comparison to immigrants or those without a fallback, which can drive relentless focus and fortitude.Signals of Early-Stage Investment: Investing at the pre-seed stage involves identifying teams with potential through their work product rather than initial conversations. Challenges of Climate Tech Investing: The difficulty in obtaining clear customer signals within climate tech is highlighted. Shaun notes that genuine customer commitment is hard to gauge and is essential for moving beyond pilot projects.Weathering the Storms: Shaun emphasizes that founders who persist through geopolitical challenges, like supply chain disruptions and tariffs, emerge uniquely stronger. The Vital Role of Communication: Regular, transparent, and honest updates from founders are crucial. Shaun believes in using structured updates to inform strategy and investment decisions, shedding light on what is and isn't working.Navigating the Path to Profitability: Shaun shares Third Sphere's model of aiming for break-even by Series A, emphasizing the value of financial independence and sustainable growth over solely seeking further rounds of venture capital.The Future of Hardware and Climate Tech: With advancements in robotics and climate resilience, the potential for transformative business opportunities in these sectors excites Shaun. Quote of the Show:“Portfolio math is brutal because it basically says that most companies don’t matter… it’s very easy to say, it’s very hard for founders to accept they may not be that one or two companies." - Shaun AbrahamsonLinks:LinkedIn: https://www.linkedin.com/in/shaunabe/ Website: https://thirdsphere.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 #ThirdSphereChapters:00:00 Intro01:30 Burned Bridges Mindset03:47 Early Bets And Bad Logos06:20 YC Founder Signal Noise08:48 Work Product Over Pitch11:32 Climate Hardware Realities15:39 Lego Building To Revenue17:29 Tariffs And Supply Chain Chaos20:02 Founders Forged By Turmoil23:54 Why Third Sphere Went Climate26:29 Mission Driven Founder Support27:26 Belief And Reality Checks30:41 Direct Feedback As A VC35:35 Private Credit Replaces Banks39:15 Founder Updates And Trust44:29 Portfolio Math Harsh Truths49:09 Biggest Missed Deal50:46 Next Decade Climate Bets53:16 Outro

What makes a startup truly successful in the eyes of venture capitalists? In this episode of Not Another CEO Podcast, host David Politis sits down with Rudina Seseri, Founder and Managing Partner at Glasswing Ventures, to dive into the realm of venture capital and discuss how startup founders can better position themselves for success.From her experience with early-stage companies to her unique perspective on the dynamics of venture capital, Rudina shares invaluable lessons about the importance of execution, understanding investor expectations, and the intricacies of navigating the startup ecosystem.Takeaways: The Value of Execution: For Rudina, the key trait she seeks in founders is execution excellence. It's not just about having a vision but demonstrating the ability and hustle to deliver beyond expectations.The Misunderstood VC Role: Many founders and employees don't understand the source of venture capital. Knowing that VCs manage funds from institutions like endowments and pensions changes the stakes and expectations.Importance of Strategic Partnerships: Rudina advises founders to seek investment from firms and partners that align with their stage and needs, rather than solely pursuing big names which might not provide necessary support.Entwining Execution with AI Dynamics: With burgeoning AI ventures, execution has become even more critical in a landscape where sheer novelty sells, yet sustainable business requires much more.The Art of Quick Decision-Making: Efficiency in decision-making during early meetings can shape successful partnerships. Rudina values honesty in communicating why a VC might pass on an opportunity, emphasizing that a quick, thoughtful no is better than indecision.Sustained Support Post-Investment: At Glasswing Ventures, support continues beyond just funding, emphasizing talent acquisition, customer connections, and strategic guidance, ensuring startups grow sustainably.Negotiating with Insight: Beyond valuation, founders should focus on the terms and structure of the deal, as these determine long-term success and alignment with investors.Quote of the Show:“What have we done for them lately to deserve to expect? Yes we’ve provided capital, but that’s not enough in my book." - Rudina SeseriLinks:LinkedIn:https://www.linkedin.com/in/rudinaseseri/   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 #GlasswingVenturesChapters:00:00 Intro01:37 Ruthless Execution02:32 Spotting Hustle Fast05:38 Execution in the AI Boom07:55 Retention and Switching Costs10:08 AI Interest vs Intent13:19 AI Hype and Human Loop17:58 How VCs Decide Quickly20:39 Giving Fast Honest Nos22:54 Execution and Go To Market Gaps24:21 How VCs Support Founders27:14 Portfolio Review Cadence28:27 Why Take Board Seats33:30 Term Sheets Beyond Valuation38:17 Choosing Firm vs Partner41:29 Scaling Support With Team43:01 Why She Became an Investor45:14 Outro

How do you choose an investor you’ll still trust when things inevitably get hard?In this episode, Ian Sigalow offers a candid, unfiltered look at early-stage investing and the founder–investor relationship, including one of the most sobering truths first-time founders often learn too late: it’s far harder to unwind a bad investor than a bad marriage. Drawing from decades of experience backing companies and founders at Greycroft, Ian breaks down how great investors actually think, decide, and engage behind the scenes.Ian shares what he looks for in exceptional founders, why the explosion of startups hasn’t increased the number of true breakout winners, and why most board meetings fail to create real value. He also explains how he works with pre-seed and seed companies, what founders consistently underestimate about investor selection, and how trust, not capital, ultimately determines whether a partnership works. This episode is a must-listen for any CEO navigating fundraising or building their first long-term investor relationships. Takeaways: Master of Two Domains: Sigalow emphasizes the importance of founders who excel in both product understanding and sales, calling them "masters of two domains" who are rare and invaluable.Big Market Potentials: Ian points out the essential need for startups to target significantly large markets. In the entrepreneurial world, having the potential to scale a company to a billion-dollar business is vital.The Earned Secret: A distinctive aspect investors look for is the "earned secret." This refers to a unique insight or approach that can lead to a competitive edge. The Importance of Trust in Investor Relationships: Sigalow stresses that founders should only take money from investors they trust, highlighting the lasting nature of these partnerships. Controlling the Board Meeting: Effective CEOs maintain control over board meetings, ensuring the focus remains on strategic issues rather than getting sidetracked. Iterate with Feedback: Founders should always be open to dreaming bigger and iterating their ideas. Sigalow feels many first-time founders hold back from sharing grand visions, perhaps fearing they don’t have the right to such ambition.Quote of the Show:“A CEO should never take money from someone they don’t trust. It’s harder to get out of a bad investor than a bad marriage." - Ian SigalowLinks:LinkedIn: https://www.linkedin.com/in/iansigalow/ Website: https://www.greycroft.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 #GreycroftChapters:00:00 Intro01:32 Founder's Qualities and Market Potential03:01 The Importance of Earned Secrets03:57 Challenges in Identifying Exceptional Founders06:12 The Evolution of Venture Capital17:42 The Role of Technology in Venture Capital21:45 Focus on Early-Stage AI Investments26:40 Choosing the Right Investment Partner10:50 Onboarding Process at Greycroft27:50 The Rule of Three in Communication29:24 Key Metrics for Founders31:21 The Role of Board Meetings38:26 Understanding Venture Capital Dynamics18:46 Ian's Journey into Venture Capital48:04 Outro

How do you lead at scale when the role constantly asks you to stretch past what feels possible?In this episode, Irina Novoselsky shares the honest, vulnerable truth behind leading at the highest levels: the job isn’t about having every answer, it’s about choosing to step into roles, decisions, and moments that stretch you and reveal what you’re capable of. Irina brings deep experience from modernizing CareerBuilder and now leading Hootsuite, the world’s most widely used social media management platform trusted by millions of users. Her leadership is defined by clarity, focus, and a relentless commitment to helping people thrive through massive inflection points.Irina walks through the systems, disciplines, and mindsets that have shaped her career, from the 15-minute weekly all-hands that transformed Hootsuite’s culture, to her 100-day onboarding playbook, to redefining the company’s ICP in 10 days and doubling growth. She also breaks down how Gen Z will reshape every company’s go-to-market motion, why naivete is an early-career superpower, and how her immigrant upbringing forged the resilience she leads with today. Takeaways: Embrace Focus and Prioritization: Irina emphasizes the addictive nature of focus and its role in driving growth. By identifying core strengths and doubling down on them, businesses can achieve unparalleled success.Redefine Company Rituals: Hootsuite’s unique weekly 15-minute all-hands meeting, serves as a crucial touchpoint. It's a tightly produced session that keeps the team energized and informed.Foster Transparency and Engagement: For Irina, transparency is key. She advocates for open communication and regular Q&A sessions, encouraging feedback, even the uncomfortable truths.Focus on Your Ideal Customer Profile: Irina advises zeroing in on your ideal customers, as this focus can lead to exponential growth. By leveraging the collective insights of her team, Hootsuite defined and refined their ICP, driving successful strategic pivots.Prioritize Customer and Employee Feedback: Meeting with customers and top performers rapidly uncovers what works and what doesn’t within a company.Embrace Vulnerability and Learn Continuously: Lastly, Irina stresses the importance of vulnerability and continuous learning. From firing oneself to reassessing priorities, self-improvement remains a constant journey for effective leadersQuote of the Show:“I get scared frequently. I put myself in vulnerable moments all the time… but those are the moments when you realize you can do hard things." - Irina NovoselskyLinks:LinkedIn: https://www.linkedin.com/in/irina-novoselsky/ Website: https://www.hootsuite.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 #HootsuiteChapters:00:00 Intro01:10 Irina's Leadership Style and Hootsuite's All Hands Meetings06:53 The Importance of Transparency and Feedback08:49 First Steps as a New CEO14:27 Identifying Key Players and Cultural Carriers18:14 The Power of Focus and Prioritization23:53 Communicating with Investors and Board Members26:35 The Role of Social Media and Personal Branding28:42 Creating a Resonant Culture29:20 The Power of Social Media for CEOs30:31 Understanding Gen Z's Buying Behavior33:15 Challenges and Growth as a CEO36:18 The Importance of Vulnerability and Mentorship51:17 Transitioning from Finance to Operations54:03 Final Reflections and Advice59:04 Outro

Can experience truly make a difference in the startup world? In this episode of Not Another CEO Podcast, David Politis speaks with Vanja Josifovski, Co-Founder and CEO of Kumo, to explore the journey of leading a cutting-edge AI enterprise. From his prestigious roles at Pinterest and Airbnb to founding Kumo, Vanja shares the lessons learned, the dilemmas faced, and the excitement of turning vast amounts of relational business data into actionable predictions.Takeaways: The Importance of Co-founders: Vanja emphasizes the critical role of choosing the right co-founders. He stresses the importance of complementary skills and experiences that create a sustainable and successful leadership team.Understanding Market Adaptability: A major challenge for technical founders can be the transition to understanding the go-to-market strategies. Vanja shares the struggles of innovating while aligning with market needs and effectively communicating product value.The Journey From Idea to Reality: Vanja sheds light on how Kumo's idea sprouted from a simple yet groundbreaking aspiration to simplify the process of turning enterprise data into predictions without the complex machine learning cycle.Raising Capital in the Current Climate: Although initially easy due to Vanja's background, he warns about the “honeymoon phase” in fundraising and the necessity of making money quickly, even when resources are abundant.The Art of Unlearning: As Vanja continues his journey, he highlights unlearning as key to adapting to new challenges. The ability to let go of old practices and adopt new methodologies is vital for growth and evolution.Quote of the Show:“It’s always easier to watch somebody do things and criticize… if somebody’s watching you from the side, they’ll always find something wrong." - Vanja JosifovskiLinks:LinkedIn: https://www.linkedin.com/in/vjosifovski/  Website: https://kumo.ai/ 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 #KumoChapters:00:00 Intro01:24 The Importance of Choosing the Right Co-Founders04:44 Defining Roles Among Co-Founders06:49 Challenges of Being a CEO10:22 Hiring and Building a Team12:54 Raising Capital and Investor Relations15:21 Kumo's Product and Market Fit18:57 Pricing Models and Strategies24:28 Acquiring the First Customers28:28 The Intensity of Starting a Company at 5032:33 The Importance of Unlearning as a CEO37:13 Challenges in Go-to-Market and Fundraising39:14 Kumo's Vision for the Future42:28 From Macedonia to Silicon Valley52:54 Advice to My Younger Self53:39 Outro

How do founders navigate the intricacies of investor relationships to scale iconic companies? In this episode of Not Another CEO Podcast, David Politis speaks with Amish Jani, co-founder and partner at FirstMark Capital, about key considerations for both investors and founders in the venture ecosystem. Amish discusses his criteria for investment, the importance of understanding the 'why' behind a founder's journey, and the strategic approach to board meetings. He also sheds light on the dynamics of venture partnerships, the evolving focus of SaaS in the AI era, and the burgeoning startup ecosystem in New York City.Takeaways: The Power of the “Why”: Amish emphasizes the importance of understanding the founder’s unique perspective on their problem. The "why" behind their journey not only reveals their depth of understanding but also what drives them to pursue their vision.Investor-Entrepreneur Fit: Amish highlights that mutual compatibility and alignment of values between the investor and the entrepreneur significantly enhance the collaboration's success over a long-term journey.The Role of Trust in Board Meetings: Amish underlines the shift from treating board meetings as sales pitches to forums for discussing challenges. Developing high trust levels allows for openness and constructive problem-solving, which can propel the company forward. Adaptability and Focus as Key Ingredients for Success: While having a clear vision is significant, the ability to adapt and listen to market feedback can sometimes pivot a company to more promising directions.Product-Market Dynamic and Competitive Edge: Amish talks about the emphasis on distribution, data acquisition, and building unique advantages that distinguish companies from competitors who may quickly replicate similar functionalities.Quote of the Show:“ We're not in a control business, we're in an influence business. And if you lose someone's ears, that's just as bad as not saying something at all." - Amish JaniLinks:LinkedIn: https://www.linkedin.com/in/amishjani/ Website: https://www.firstmark.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 #FirstMarkChapters:00:00 Intro01:19 Amish’s Investment Philosophy02:38 The Importance of 'Why' in Founders03:40 Evaluating Founders and Their Vision05:08 The Role of Product and Market Understanding06:13 Challenges and Insights in Venture Capital08:30 Investor-Founder Fit and Long-Term Relationships21:07 The Importance of Choosing the Right Investor21:56 The Role of Founders in Shaping Company Culture23:09 Navigating Hard Conversations with Founders25:54 Effective Board Meetings: Moving Beyond Sales Pitches30:04 The Current State of AI and Market Dynamics37:06 The Evolution of New York's Tech Ecosystem41:26 Why Amish Became an Investor43:47 Outro

Can imposter syndrome drive you to succeed? In this solo episode of Not Another CEO Podcast, David explores his personal experiences with imposter syndrome and shares valuable insights gathered from countless conversations with leaders who have faced similar challenges.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 #FebruaryCEOPulseChapters:00:00 Intro00:51 Personal Experiences with Imposter Syndrome03:04 Defining Imposter Syndrome04:56 The Two Paths of Imposter Syndrome06:48 Channeling Imposter Syndrome for Growth09:02 Practical Advice for Dealing with Imposter Syndrome13:28 Outro

Have you ever wondered how leaders manage to scale their organizations without being involved in every intricate detail? In this week’s episode, David Politis welcomes David Karandish, Founder and CEO of Capacity. Together, they delve into the art of building compound startups, scaling intricately interconnected businesses, and the profound role AI plays in today's market dynamics.David introduces the idea of building "machines" within your organization. While this doesn't refer to physical machines, it's about creating efficient processes that can operate independently of constant human intervention. Takeaways: The Compound Startup Strategy: David Karandish introduces the concept of a "compound startup," a term coined by Parker Conrad that he has effectively applied at Capacity. The premise revolves around integrating various point solutions into a cohesive platform, reducing costs while maximizing the bundle's value.Navigating Mergers and Acquisitions: Handling 14 company acquisitions in just three years, David shares his approach to successful mergers. He emphasizes the importance of each acquisition fitting into the broader company mission, fostering synergy rather than assembling a mere collection of brands.Building Machines in Business Processes: David advocates for creating “machines,” repeatable processes that enhance efficiency and scalability within an organization. Impact of AI on Business Operations: The discussion highlights the evolving landscape of AI solutions. While initial efforts centered around point solutions, the trend is shifting towards platform consolidation.The Role of Communication Frameworks: David reflects on how establishing a structured cadence for goal setting and meetings has been vital at Capacity, ensuring alignment across 350+ employees worldwide.Cultivating Entrepreneurial Ecosystems: David discusses his commitment to fostering entrepreneurial growth within St. Louis. Despite the city's historical challenges in securing late-stage funding, there is a burgeoning potential with the rise of local talent and incubation initiatives, ultimately aiming to transform St. Louis into a thriving tech hub.Quote of the Show:“By machine, I don't necessarily mean how you think like a physical idea, but I mean more repeatable processes that scale and remove as much human decision making outta the process as possible." - David KarandishLinks:LinkedIn: https://www.linkedin.com/in/davidkarandish/Website: https://capacity.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 #CapacityChapters:00:00 Intro01:43 The Concept of a Compound Startup04:09 Strategic Acquisitions and Integrations05:41 Challenges and Solutions in M&A09:24 The AI Revolution and Market Trends13:01 Implementing EOS and Organizational Frameworks17:38 Building and Operating Effective Machines21:12 Hiring for Stage Fit and Problem Solving27:57 St. Louis Entrepreneurial Scene33:39 AI and Market Noise38:53 Big Breaks and Business Models41:28 Managing Energy and Time43:34 Balancing Work and Family47:35 Advice for Aspiring Entrepreneurs48:31 Outro

How do you know if a company is actually building momentum, or just looking polished on the surface? In this episode of Not Another CEO Podcast, David sits down with Jeff Morris Jr., Founder and General Partner at Chapter One, to break down what truly matters at the earliest stages of building a company. Jeff invests at pre-seed and seed, where ambiguity is high, data is limited, and speed of learning is often the only real signal. Before becoming an investor, Jeff was an early product leader at Tinder, helping scale the product to hundreds of millions of users, an experience that deeply shapes how he evaluates founders today.Jeff shares how he thinks about product velocity, founder self-awareness, team dynamics, and why the individual partner matters far more than the firm logo. This conversation is a masterclass for CEOs building from zero to one and choosing who they want in the trenches with them. Takeaways: Product Velocity Matters: Jeff emphasizes the importance of product velocity, especially in the early stages of a startup. He explains that founders need to run numerous experiments to achieve product-market fit, often partnering with technical leaders to accelerate this process.Building the Right Team: According to Jeff, a strong indication of a founder's potential is their ability to attract a talented team. He believes that successful founders often draw in colleagues from their previous ventures, creating a "band" that's been together through various challenges.The Sales Dilemma: Founders with technical expertise often lack strong sales skills. Jeff looks for self-awareness in founders, assessing if they can identify their weaknesses and augment them with the right partners or co-founders.The Importance of Early Impressions: First impressions are crucial in the VC world. Jeff and David both agree that initial meetings often determine whether an investor leans in. Founders should craft a compelling story and use the first few minutes to capture interest.Aligning with the Right Investor: For Jeff, investing is akin to a decade-long partnership. He advises founders to seek investors who align with their vision and are genuinely interested in their success, rather than just providing capital.Preparation and Self-Awareness: Founders need to be brutally honest about their strengths and weaknesses. Jeff advises preparing thoroughly before meeting investors and leveraging one's unique strengths while addressing weaknesses to form a complete leadership package.Quote of the Show:“We talk a lot about product velocity being the most critical metric we look for." - Jeff Morris Jr.Links:LinkedIn: https://www.linkedin.com/in/jeffmorrisjr/ Website: https://chapterone.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 #ChapterOneChapters:00:00 Intro01:10 Key Metrics for Early-Stage Investments02:37 Assessing Founders and Teams07:51 The Importance of Self-Awareness in Founders10:38 The Founder-Investor Relationship14:34 Navigating the Venture Capital Landscape19:12 The Dynamics of Fundraising27:36 The Current Investment Climate41:44 Jeff Morris, Jr.'s Journey to Venture Capital44:39 Outro

How do you create a work culture that stands out and inspires team loyalty across multiple companies? In this episode, we gain valuable insights on this and more from the illustrious career of Donna Dubinsky. Known for her pivotal roles at Palm Computing and Handspring, Donna offers a rare long-term perspective on leadership, culture, and the technological landscape that has spanned decades. Takeaways: The Importance of Building a Strong Culture: Donna emphasizes that a great company starts with great people. She shares the crucial role a positive culture played in her companies, stating that when you foster an environment people love, they follow you from venture to venture.Adaptability is Key: One of the most sought-after traits in employees, according to Donna, is flexibility. She highlights the importance of hiring individuals who are not rigid in their thinking but can pivot and grow with the company.Challenges of Raising Capital: Donna recounts the struggles in securing investment for Palm, despite her extensive network. She faced skepticism from investors due to previous failures in handheld computing and the prioritization of internet ventures over hardware.Reflective Organizational Planning: Donna shares her strategic approach to planning through biannual offsites, fostering a culture of reflection and adjustment. These sessions not only solidified strategic objectives but also enhanced team camaraderie through collaborative efforts and fun activities.Maintaining Integrity and Respect: Donna’s overarching advice is to treat everyone with respect. This principle was foundational in building the cultures of her companies and remains a critical lesson for sustainable leadership.Quote of the Show:“I really appreciated people who could deal with change. Changing circumstances, changing environment, changes within the company, as opposed to people who were rigid." - Donna DubinskyWays 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 #Handspring #PalmChapters:00:00 Intro01:30 The Importance of People in Building Companies03:42 Creating and Maintaining Company Culture16:00 The Palm Story: Revolutionizing Personal Computing37:09 Frustrations of Being an Employee37:44 Challenges of Selling a Company39:02 Balancing Structure in Big Companies40:55 Starting Handspring and Product Focus45:03 Biggest Mistake at Handspring49:00 Advice for Fast-Growing Companies50:28 Impact of AI and Market Dynamics55:05 Personal Background and Career Beginnings57:33 Big Breaks and Mentorship01:03:06 Government Service and National Impact01:07:49 Outro

How do great founders use their best moments, not their hardest ones, to build the future of their company?In this episode, Jules Maltz shares the mindset that has guided him through decades of backing generational companies like Slack, Dropbox, Grammarly, MuleSoft, G2, and Buddy Media. For Jules, the brightest periods in a company’s journey are the moments to build aggressively: to hire exceptional executives, deepen product moats, and prepare for act two and act three long before the market forces the issue.Jules also opens up about what he looks for in founders, why authenticity matters more than pitch polish, and how trust is built in the first months of an investor–founder relationship. He reflects on his own misses, the evolution of venture capital, and the emotional clarity that underpins his earliest investment decisions.  Takeaways: Authenticity and Passion are Essential: Jules emphasizes the importance of authenticity and passion in founders. He looks for individuals who have a genuine drive and a personal connection to the problem they are solving.Beyond the Metrics: When evaluating potential investments, Jules seeks stories that transcend traditional metrics. He recalls his first investment in Twitter, where the pitch focused more on the transformative potential of the platform rather than immediate financial returns.Building Trust Early On: Establishing trust during the initial months after an investment is crucial. Jules believes that consistently delivering on promises and being genuinely helpful builds credibility.Adapting Communication Styles: Jules adapts his communication style based on the needs of each CEO. Some prefer regular updates, while others might communicate only during key events.Sustaining Growth Through Strategic Hiring: Jules advises companies to recruit strong executives and think ahead about their business strategies during periods of growth. By doing so, businesses can better navigate market changes and sustain their growth trajectory.Nurturing Relationships for Long-Term Success: Relationships are at the heart of venture capital. Whether it's trust between founders and investors or maintaining connections with past business partners, nurturing these relationships can lead to long-term success and learning.Quote of the Show:“When the sun is shining on your business, that’s a great time to recruit super strong executives and think about act two and act three." - Jules MaltzLinks:LinkedIn: https://www.linkedin.com/in/julesmaltz/ Website: https://www.ivp.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 #IVPChapters:00:00 Intro01:25 Key Traits of Successful Founders03:52 The Importance of Authenticity06:17 Evaluating Investment Opportunities10:59 The Twitter Investment Story21:57 Building Trust with Founders27:11 Trusting Your CEO's Vision29:31 Navigating Hypergrowth and Market Changes33:53 The Excitement and Challenges of AI Investments41:51 Teaching and Sharing Venture Capital Insights47:24 The Role of Trust in Venture Capital50:35 Biggest Investment Regrets53:31 Outro

How can you get the most out of your year-end? In this solo episode of Not Another CEO Podcast, David explores how leaders can leverage the end of the year for reflection, rallying their troops, and recharging for what lies ahead.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 #DecemberCEOPulseChapters:00:00 Intro01:22 Reflect: Assessing Achievements05:15 Rally: Energizing Your Team11:14 Recharge: Taking Time to Rest13:33 Outro

How do you keep building when every month your company is almost out of money, and quitting would be the logical choice?In this episode, Artem Rodichev shares the gritty, unfiltered story of Ex Human’s near-death year. Instead of shutting the company down, that year hardened the team, shaped the culture, and created a level of resilience that became Ex Human’s defining advantage.Now Ex Human is profitable and building empathetic AI characters capable of multimodal emotional intelligence, technology designed to see, hear, and feel in ways that help combat loneliness. Artem also discusses his path from leading AI at Replica to building a company that spans both consumer and enterprise markets, powered by millions of user-created AI characters that generate a unique data advantage.  Takeaways:Persistent Belief in Your Vision: Artem emphasized the importance of having unwavering belief in your mission. His steadfast belief in the potential of AI to create meaningful human interactions kept him going through challenging times.Foster a Culture of Resourcefulness and Persistence: The trials that Ex Human endured became pivotal learning experiences, instilling a culture of resourcefulness and persistence within the team. Be Prepared for Sacrifices: Artem candidly discussed the personal sacrifices he made, including taking a salary below market rate and making hard personnel decisions. Expand Beyond Comfort Zones: Despite an engineering background, Artem knew he needed to step out of his comfort zone and learn essential skills like marketing and sales to lead Ex Human effectively.Data-Driven Innovation: Ex Human’s success hinges on continuously refining their AI models with data collected from their consumer app. This iterative approach allows them to stay ahead in the competitive AI market.Transitioning from a Stable Job to Entrepreneurship: Artem’s move from a significant role at Replica to founding his startup showcases the courage needed to leave stability behind in pursuit of a bigger vision.Quote of the Show:“Every month I thought I should give up. But then the other side of me said, if you give up now, you’ll never build the future you believe in." - Artem RodichevLinks:LinkedIn: https://www.linkedin.com/in/art-rodichev/ Website: https://exh.ai/#home 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 #ExHumanChapters:00:00 Intro01:24 The Importance of Persistence04:33 Belief in the Vision05:53 Personal Sacrifices and Company Culture11:07 Solo Founder Challenges12:29 Building a Strong Team14:45 The Role of a Founder18:47 Consumer AI and Empathetic Companions29:41 Breaking Inertia: Leaving a Successful Company32:06 Limitations and New Opportunities: The Birth of a New Venture34:50 B2C and B2B: Balancing Two Markets37:11 The Importance of Data in AI Development42:28 Challenges and Competitions in the AI Market49:41 Personal Background: From Kazakhstan to Tech Entrepreneurship57:00 Final Reflections and Advice for Aspiring Entrepreneurs58:39 Outro

How do you scale a company from zero to $100 million in 18 months without losing quality, clarity, or control?In this episode, Matt Price shares the remarkable story of building Crescendo, one of the fastest-growing companies ever featured on the show, by reimagining customer experience through advanced AI and deeply trained specialists. Matt’s journey has come full circle: from a technical support rep early in his career, to scaling Zendesk, to now creating an entirely new model for enterprise-grade customer care.Matt opens up about assembling an elite leadership team in record time, creating a vertically integrated product-and-operations engine, and designing a culture anchored around accountability, curiosity, and constant communication. He also explains why outcome-based pricing changes everything, how General Catalyst’s creation model gave Crescendo an unfair advantage, and why traditional BPOs simply aren’t positioned for the AI era. This is a masterclass in speed, focus, and operational excellence. Takeaways:Building a Stellar Team: Matt emphasized the importance of assembling a high-quality team quickly. He discussed how bringing in top talent, especially those with experience in related fields, has been crucial for Crescendo's rapid growth.Curiosity and Vision as Key Attributes: When recruiting for a fast-growth environment, Matt values curiosity and passion for the company's vision. These attributes, combined with relevant experience, are critical for innovation and progress.Prioritizing Outcomes Over Traditional Models: Crescendo has embraced outcome-based pricing, aligning the company’s success with customer satisfaction. This model contrasts with traditional seat-based pricing and encourages the entire organization to focus on end-to-end service quality.Integrating AI Thoughtfully: Matt spoke about the evolution of AI in customer care and its potential to transform the industry. By integrating AI with human expertise, Crescendo offers enhanced support experiences.Strategic Acquisition for Growth: The strategic acquisition of traditional BPOs has allowed Crescendo to expand its distribution and offer scalable AI solutions. Matt's approach underscores the power of mergers and acquisitions in achieving rapid growth.Creating a Culture of Accountability: Matt stressed the significance of having someone accountable for leading every project or initiative. In a fast-paced environment, clarity in roles and responsibilities is vital for efficiency and progress.Fostering Open Communication: Maintaining open communication channels, even in remote settings, is a priority for Crescendo's leadership. Matt ensures his team stays connected through regular meetings and an open-door policy.Quote of the Show:“Customer care was constrained by the economics. In order to deliver customer care up to now, you have to put humans in, a lot of people in… and AI now changes that, AI puts us into a world of abundance. And we need to shift our mindsets now as CX leaders… we’re moving from being deflectors to creators and innovators." - Matt Price Links:LinkedIn: https://www.linkedin.com/in/growthspecialist/ Website: https://www.crescendo.ai/ 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 #CrescendoChapters:00:00 Intro01:32 Building a High-Impact Team03:40 The Role of AI in Customer Service06:03 Rapid Growth and Company Evolution07:58 Leadership and Team Dynamics11:03 AI Integration and Product Development21:53 Founding Crescendo and Market Opportunities28:10 Challenges and Focus as a CEO31:08 The CEO's Influence on Team Dynamics35:00 Outcome-Based Pricing in SaaS36:22 Challenges and Benefits of Outcome-Based Models41:25 Strategic Growth Through Acquisitions47:04 The Future Vision for Crescendo48:34 Personal Journey and Early Career58:33 Advice for Aspiring Entrepreneurs59:29 Outro

Have you ever wondered what it takes to build a company from your garage to a public entity?In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public company CEO, and the reality that even the strongest operators can’t outrun macro cycles.Chieh also opens up about what happens after the final chapter closes, the exhaustion, the identity shift, and the unexpected necessity of real recovery. His honesty about the highs, lows, and lessons he’s taking into his next company makes this a powerful episode for founders navigating their own versions of the broken-glass analogy. Takeaways: From Humble Beginnings to a Notable Success: Chieh Huang started Boxed in 2013 right from his garage, with only dreams and a strong will to succeed. Within a few years, Boxed scaled to become a renowned online wholesale retailer, serving millions.The Challenge of Maintaining Purpose: Chieh emphasizes the importance of cultivating an intrinsic purpose within a company. At Boxed, the sense of purpose wasn’t predefined but evolved over time as the team grew, particularly among the fulfillment center workers.The Rollercoaster Ride of Fundraising: Chieh's journey wasn't without financial hurdles. While initial investments were relatively easier owing to his prior success in the gaming industry, subsequent rounds posed challenges, reflecting the inconsistent nature of venture funding.Consumer Business Dynamics: Chieh discusses the unpredictability of consumer businesses, highlighting how a single viral moment or endorsement can drastically influence a company's success, unlike enterprise businesses that grow through steady acquisition of clients.Public Company Experience: Huang's experience in taking Boxed public via a SPAC (Special Purpose Acquisition Company) taught him that public market dynamics significantly differ from private venturesHandling Burnout: Chieh and David discuss the inevitability of burnout in an entrepreneur's journey and the importance of managing it proactively through short breaks, personal downtime, and stepping away when necessary to recharge.Quote of the Show:“Being a CEO is like trying to be the greatest of all time in a broken glass eating competition." - Chieng HuangLinks:LinkedIn: https://www.linkedin.com/in/chiehhuang/ Website: https://boxed.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 #BoxedChapters:00:00 Intro00:46 The Journey of Boxed02:42 The Purpose Behind Boxed07:14 Starting in the Garage09:23 The Big Break and Rapid Growth20:36 Fundraising Challenges and Successes26:02 Navigating Market Ups and Downs32:09 Reflecting on Past Experiences33:59 Journey to Going Public36:26 Challenges of Being a Public Company CEO39:22 Navigating Investor Relationships44:17 Balancing Work and Avoiding Burnout50:03 The End of Boxed and New Beginnings55:03 Early Entrepreneurial Spirit57:54 Role Models and Mentors01:01:25 Core Motivations and Advice01:05:51 Outro

When was the last time you paused long enough to thank the people who quietly helped you build?In this special compilation episode, we highlight moments from eleven CEOs who reflected on the investors that shaped their companies’ trajectories, not just through capital, but through conviction, guidance, and belief. These clips reveal how the right investors help founders stay grounded in their mission, navigate uncertainty, and make better decisions during pivotal moments of growth.Across these stories, one theme stands out: exceptional investors don’t just finance a business, they help founders become better leaders. They open doors, challenge thinking, and offer support that often goes unspoken and uncelebrated. As we head into the holiday season, this episode is an invitation for CEOs to pause, reflect, and acknowledge the people whose partnership made the climb possible.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 Chapters:00:00 Intro02:17 Daniel Chait - Greenhouse02:54 Kyle Porter - Salesloft06:50 Craig Walker - Dialpad13:24 Dane Atkinson - Odeko21:11 Diego Oppenheimer - Algorithmia24:46 Itamar Friedman - Qodo28:43 Jeron Paul - Spiff34:03 Nadia Boujarwah - Dia&Co38:59 Nick Patrick - Radar44:16 Toby Kraus - Lightship53:30 Tom Buiocchi - ServiceChannel54:09 Outro

How can you motivate your team to embrace AI in their daily work? In this solo episode of Not Another CEO Podcast, David discusses strategies to drive an AI-first mindset in your company.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 #NovemberCEOPulseChapters:00:00 Intro03:16 Get Your Team Using AI06:24 Get Traction With Focused AI Projects10:42 Install A Champion To Own AI14:00 Outro

How do you build one of the fastest-growing integration platforms in tech, while keeping culture, momentum, and innovation in sync?In this episode, Shensi Ding, Co-Founder and CEO of Merge, shares her journey from investment banking to leading one of the most successful integration infrastructure companies in the market. She opens up about the company’s evolution, from a small startup in San Francisco to a category leader powering technology products and AI agents for companies like Ramp and OpenAI.Shensi also discusses how she built Merge’s in-person culture during the height of the pandemic, what it takes to recruit top talent, and the lessons she’s learned about decision-making, adaptability, and sustaining momentum as a founder. Takeaways: The Importance of Company Culture: Shensi emphasizes the significance of maintaining an in-person culture at Merge, even amidst the challenging conditions of the COVID-19 pandemic.Maintaining Quality Over Competing on Price: Shensi discusses the challenge of maintaining a premium product in an environment saturated with copycats. She was inspired by the CEO of Gong, who reinforced that a company cannot be both the best and the cheapest.Navigating Growth and Innovation: An integral part of Merge's ethos has been to constantly innovate and adapt, which Shensi highlights by discussing the launch of new products and their strategic shifts towards AI-driven solutions.Integration and Expansion as Key Growth Drivers: Shensi highlights the significance of diversifying Merge’s product offerings and expanding into new markets to drive growth. By strategically adding categories and aiming for enterprise-level clients, Merge has expanded its market reach and increased its potential for acquiring larger clients.Lessons in Leadership and Adaptability: David and Shensi discuss the value of learning from industry veterans and mentors, which Merge facilitates by inviting successful leaders to speak with their team.Navigating Fundraising and Investor Relations: In discussing fundraising experiences, Shensi highlights the importance of clear differentiation and conveying the unique value of your product to investors. While the initial seed round was challenging, securing well-known investors early on eased future fundraising efforts.Quote of the Show:“You can’t be the best and the cheapest. You need to decide what you want to be." - Shensi DingLinks:LinkedIn: https://www.linkedin.com/in/shensiding/ Website: https://www.merge.dev/ 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 #MergeChapters:00:00 Intro01:40 Starting Merge During the Pandemic02:50 Challenges of In-Person Work Culture03:42 Expanding to New York and International Markets04:50 Maintaining Work Ethic and Decision Making06:42 Evolving Leadership and Learning from Mistakes10:56 Bringing Industry Leaders to Inspire the Team13:56 Acquiring the First Customers16:38 Dealing with Copycats and Maintaining Quality21:08 Product Evolution and Adapting to AI27:59 The Halo Effect of New Products29:59 Promoting AI Tools Internally33:15 Fundraising Challenges and Successes38:08 Moving Upmarket and Adapting41:42 Founders' Background and Journey47:16 Balancing Work and Personal Life50:41 Outro

How do the best founders learn faster, think deeper, and turn that mindset into companies that endure for decades?In this episode, host David Politis sits down with Nikhil Basu Trivedi, Co-Founder of Footwork, one of Silicon Valley’s most respected early-stage investors. Nikhil’s career spans both sides of the table, from co-founding Artsy, the groundbreaking online art platform, to investing in category-defining companies like Canva, Lattice, Frame.io, and The Farmer’s Dog.Nikhil shares how he evaluates founders, why the “slope of learning” is the most important quality he looks for, and how he builds long-term partnerships based on trust, curiosity, and shared ambition. He also opens up about the changing venture landscape, the hype and opportunity of AI, and what it means to be an investor who has truly walked in a founder’s shoes.Understanding the Importance of Learning: Nikhil emphasized the significance of the "slope of learning" in evaluating founders. This refers to a founder's ability to quickly learn and adapt to evolving market conditions, especially in the fast-paced AI era.Making a Lasting First Impression: According to Nikhil, the first few minutes with a potential investor are critical. Whether it's 15 or 30 minutes, founders must capture the investor's attention and highlight their vision's potential.Pitching with Conviction: Nikhil advised founders to clearly articulate why their business has the potential to be massive. It's crucial to strike a balance between ambition and grounded reality.Value of Ongoing Communication: Post-investment, Nikhil stressed the importance of maintaining regular communication between founders and investors. Leveraging AI for Better Investments: Footwork has been proactive in using AI to manage and analyze portfolio companies, allowing them to track company progress and trends efficiently.Empathy from Experience: As a former operator and founder, Nikhil shared his belief that empathy is crucial in the investor-founder relationship. Understanding the challenges founders face allows investors like Nikhil to be better partners, offering thoughtful guidance rather than prescriptive advice.Quote of the Show:“In the first 30 minutes with a founder, I’m trying to assess their slope of learning… We invest in slope, not just smarts. How fast a founder learns matters more than what they know on day one." - Nikhil Basu TrivediLinks:LinkedIn: https://www.linkedin.com/in/nikhilbt/ Website: https://www.footwork.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 #Footwork Chapters:00:00 Intro01:27 Key Traits in Founders: The Slope of Learning04:59 The Importance of First Impressions in Pitching13:48 Evaluating and Supporting Portfolio Companies19:44 The Impact of AI on Venture Capital24:04 The Value of Thought Partnership31:10 Reflections on Missed Opportunities and Career Choices36:30 Future Aspirations for Footwork 38.25 Outro