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 #FebruaryCEOPulse

Chapters:

00:00 Intro

00:51 Personal Experiences with Imposter Syndrome

03:04 Defining Imposter Syndrome

04:56 The Two Paths of Imposter Syndrome

06:48 Channeling Imposter Syndrome for Growth

09:02 Practical Advice for Dealing with Imposter Syndrome

13:28 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 Karandish

Links:

• 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 #Capacity

Chapters:

00:00 Intro

01:43 The Concept of a Compound Startup

04:09 Strategic Acquisitions and Integrations

05:41 Challenges and Solutions in M&A

09:24 The AI Revolution and Market Trends

13:01 Implementing EOS and Organizational Frameworks

17:38 Building and Operating Effective Machines

21:12 Hiring for Stage Fit and Problem Solving

27:57 St. Louis Entrepreneurial Scene

33:39 AI and Market Noise

38:53 Big Breaks and Business Models

41:28 Managing Energy and Time

43:34 Balancing Work and Family

47:35 Advice for Aspiring Entrepreneurs

48:31 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 #ChapterOne

Chapters:

00:00 Intro

01:10 Key Metrics for Early-Stage Investments

02:37 Assessing Founders and Teams

07:51 The Importance of Self-Awareness in Founders

10:38 The Founder-Investor Relationship

14:34 Navigating the Venture Capital Landscape

19:12 The Dynamics of Fundraising

27:36 The Current Investment Climate

41:44 Jeff Morris, Jr.'s Journey to Venture Capital

44:39 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 Dubinsky

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 #Handspring #Palm

Chapters:

00:00 Intro

01:30 The Importance of People in Building Companies

03:42 Creating and Maintaining Company Culture

16:00 The Palm Story: Revolutionizing Personal Computing

37:09 Frustrations of Being an Employee

37:44 Challenges of Selling a Company

39:02 Balancing Structure in Big Companies

40:55 Starting Handspring and Product Focus

45:03 Biggest Mistake at Handspring

49:00 Advice for Fast-Growing Companies

50:28 Impact of AI and Market Dynamics

55:05 Personal Background and Career Beginnings

57:33 Big Breaks and Mentorship

01:03:06 Government Service and National Impact

01:07:49 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 Maltz

Links:

• 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 #IVP

Chapters:

00:00 Intro

01:25 Key Traits of Successful Founders

03:52 The Importance of Authenticity

06:17 Evaluating Investment Opportunities

10:59 The Twitter Investment Story

21:57 Building Trust with Founders

27:11 Trusting Your CEO's Vision

29:31 Navigating Hypergrowth and Market Changes

33:53 The Excitement and Challenges of AI Investments

41:51 Teaching and Sharing Venture Capital Insights

47:24 The Role of Trust in Venture Capital

50:35 Biggest Investment Regrets

53:31 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 #DecemberCEOPulse

Chapters:

00:00 Intro

01:22 Reflect: Assessing Achievements

05:15 Rally: Energizing Your Team

11:14 Recharge: Taking Time to Rest

13:33 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 Rodichev

Links:

• 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 #ExHuman

Chapters:

00:00 Intro

01:24 The Importance of Persistence

04:33 Belief in the Vision

05:53 Personal Sacrifices and Company Culture

11:07 Solo Founder Challenges

12:29 Building a Strong Team

14:45 The Role of a Founder

18:47 Consumer AI and Empathetic Companions

29:41 Breaking Inertia: Leaving a Successful Company

32:06 Limitations and New Opportunities: The Birth of a New Venture

34:50 B2C and B2B: Balancing Two Markets

37:11 The Importance of Data in AI Development

42:28 Challenges and Competitions in the AI Market

49:41 Personal Background: From Kazakhstan to Tech Entrepreneurship

57:00 Final Reflections and Advice for Aspiring Entrepreneurs

58:39 Outro