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

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 ventures
• Handling 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 Huang

Links:

• 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 #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

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 Intro

02:17 Daniel Chait - Greenhouse

02:54 Kyle Porter - Salesloft

06:50 Craig Walker - Dialpad

13:24 Dane Atkinson - Odeko

21:11 Diego Oppenheimer - Algorithmia

24:46 Itamar Friedman - Qodo

28:43 Jeron Paul - Spiff

34:03 Nadia Boujarwah - Dia&Co

38:59 Nick Patrick - Radar

44:16 Toby Kraus - Lightship

53:30 Tom Buiocchi - ServiceChannel

54:09 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 #NovemberCEOPulse

Chapters:

00:00 Intro

03:16 Get Your Team Using AI

06:24 Get Traction With Focused AI Projects

10:42 Install A Champion To Own AI

14:00 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 Ding

Links:

• 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 #Merge

Chapters:

00:00 Intro

01:40 Starting Merge During the Pandemic

02:50 Challenges of In-Person Work Culture

03:42 Expanding to New York and International Markets

04:50 Maintaining Work Ethic and Decision Making

06:42 Evolving Leadership and Learning from Mistakes

10:56 Bringing Industry Leaders to Inspire the Team

13:56 Acquiring the First Customers

16:38 Dealing with Copycats and Maintaining Quality

21:08 Product Evolution and Adapting to AI

27:59 The Halo Effect of New Products

29:59 Promoting AI Tools Internally

33:15 Fundraising Challenges and Successes

38:08 Moving Upmarket and Adapting

41:42 Founders' Background and Journey

47:16 Balancing Work and Personal Life

50:41 Outro