Episode 29: "Values On Our Sleeve" | Liberty Ventures Founder Alexander McCobin On Values-Forward Capital Allocation, Building Authentic Communities, And Why Great Events Are 100% Worth The Effort The Diligent Observer podcast

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Episode 29: "Values on Our Sleeve" | Liberty Ventures Founder Alexander McCobin on Values-Forward Capital Allocation, Building Authentic Communities, and Why Great Events are 100% Worth the Effort

6M ago 43:21

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Insights from a former philosophy student who's built a 15,000+ member network of principled business leaders and facilitated values-aligned investments

Today's episode explores 3 ideas that caught my attention:

The power of a radically transparent thesis - Alexander's approach of explicitly stating values upfront both attracts aligned founders and repels mismatches.
Patient capital as competitive advantage - His willingness to build relationships over months/years before investing challenges the all-too-common "FOMO" mindset. Slowing down can lead to better decisions.
Events as ecosystem catalyst - Liberty Ventures uses gatherings to enhance their thesis and build a stronger community, not just for deal flow. A vital lesson for investor communities that highlights the value of consistent connection.

I explore these ideas and more with Alexander McCobin, Founder of Liberty Ventures. He's building the largest network of values-aligned investors and entrepreneurs committed to advancing capitalism as a force for good, drawing on his experience leading both Students For Liberty and Conscious Capitalism.

During our conversation, Alexander shares:

Why typical "quick close" pressure often leads to suboptimal decisions - illustrated through specific examples of relationship-based investing.
How conscious capitalism principles shape investment strategy - detailed through Liberty Ventures' approach to building aligned ecosystems.
Practical approaches to running investor events - including specific tactics for starting small and finding the right partners.

Connect with Alexander
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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Chapters

1. Introduction (00:00:00)

2. Excitement for 2025 and Innovation (00:01:58)

3. Examples of Entrepreneurial Energy (00:02:42)

4. Conscious Capitalism Explained (00:04:07)

5. Alexander's Journey to Conscious Capitalism (00:04:17)

6. Founding Liberty Ventures (00:13:46)

7. Investment Philosophy and Deal Flow (00:15:25)

8. Evaluating Founders and Companies (00:19:54)

9. Maintaining Values in Business (00:23:08)

10. Building a Community of Values-Aligned Leaders (00:26:16)

11. Advice for Growing Angel Communities (00:30:38)

12. Maintaining Values in Business Growth (00:32:15)

13. Learning from Missed Investments (00:40:43)

56 episodes