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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
LinkedIn | X | Website
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Connect with Andrew
LinkedIn | X | Angel Ops E-Book
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)
49 episodes
