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