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Mastering the Art of Fundraising: Insights from Redbud VC's Brett Calhoun

In this episode of Allstar Allocator, host Austin Jia sits down with Brett Calhoun, managing general partner at Redbud VC, to delve into the challenges and strategies behind successful fundraising. Discover Brett's journey, including his appearance on the Forbes 30 Under 30 list, his approach to investing in resilient entrepreneurs, and how he evaluates potential investments. Whether you're a startup founder or a fund manager, this conversation offers invaluable insights into the art of raising capital, evaluating founders, and navigating the complex landscape of venture capital.

00:00 Introduction to Fundraising Challenges
00:15 Meet Brett Calhoun: Venture Capitalist Extraordinaire
00:58 Redbud VC's Investment Philosophy
01:38 The Importance of Resilience in Founders
03:03 Evaluating Early-Stage Startups
03:50 Unique Approaches to Due Diligence
06:27 Balancing Operator and Investor Perspectives
11:20 Portfolio Construction Strategies
13:56 Fundraising for Venture Capital Firms
16:32 Fundraising Timeline and Strategy
17:48 Fundraising Journey and Challenges
18:24 Cold vs. Warm Investor Relationships
19:01 Networking and Securing Key Investors
21:27 Fundraising Strategies and Follow-ups
23:23 Industry Insights and AI Trends
26:55 Evaluating Investment Opportunities
30:03 Quickfire Questions and Personal Insights