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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.
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Chapters:
00:00 Intro
01:19 Amish’s Investment Philosophy
02:38 The Importance of 'Why' in Founders
03:40 Evaluating Founders and Their Vision
05:08 The Role of Product and Market Understanding
06:13 Challenges and Insights in Venture Capital
08:30 Investor-Founder Fit and Long-Term Relationships
21:07 The Importance of Choosing the Right Investor
21:56 The Role of Founders in Shaping Company Culture
23:09 Navigating Hard Conversations with Founders
25:54 Effective Board Meetings: Moving Beyond Sales Pitches
30:04 The Current State of AI and Market Dynamics
37:06 The Evolution of New York's Tech Ecosystem
41:26 Why Amish Became an Investor
43:47 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:
#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.
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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.
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Ways to Tune In:
#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:
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Ways to Tune In:
#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.
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Ways to Tune In:
#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:
#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:
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Ways to Tune In:
#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
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.
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#NotAnotherCEO #BusinessSuccess #Crescendo
Chapters:
00:00 Intro
01:32 Building a High-Impact Team
03:40 The Role of AI in Customer Service
06:03 Rapid Growth and Company Evolution
07:58 Leadership and Team Dynamics
11:03 AI Integration and Product Development
21:53 Founding Crescendo and Market Opportunities
28:10 Challenges and Focus as a CEO
31:08 The CEO's Influence on Team Dynamics
35:00 Outcome-Based Pricing in SaaS
36:22 Challenges and Benefits of Outcome-Based Models
41:25 Strategic Growth Through Acquisitions
47:04 The Future Vision for Crescendo
48:34 Personal Journey and Early Career
58:33 Advice for Aspiring Entrepreneurs
59:29 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:
Quote of the Show:
Links:
Ways to Tune In:
#NotAnotherCEO #BusinessSuccess #Boxed
Chapters:
00:00 Intro
00:46 The Journey of Boxed
02:42 The Purpose Behind Boxed
07:14 Starting in the Garage
09:23 The Big Break and Rapid Growth
20:36 Fundraising Challenges and Successes
26:02 Navigating Market Ups and Downs
32:09 Reflecting on Past Experiences
33:59 Journey to Going Public
36:26 Challenges of Being a Public Company CEO
39:22 Navigating Investor Relationships
44:17 Balancing Work and Avoiding Burnout
50:03 The End of Boxed and New Beginnings
55:03 Early Entrepreneurial Spirit
57:54 Role Models and Mentors
01:01:25 Core Motivations and Advice
01:05:51 Outro
From the publisher's feed
Our mission is to bend the curve for Founders and CEOs. At Not Another CEO, we know there’s no formula for running a business. Leadership is forged through unique journeys, real challenges, and…

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