E1055: Hustle Fund Co-Founder & General Partner Elizabeth Yin on her unique portfolio strategy, attracting first-time LPs, optimism for post-COVID fundraising, dealing with pro rata as a smaller fund & more!

0:50 Jason opens the show with some thoughts on livelihood, getting back to work as a lose-lose situation and approaching the situation with kindness and empathy 5:47 Jason intros Hustle Fund's Elizabeth Yin and they discuss the process of raising Hustle Fund I and targeting first-time LPs 10:25 Why high net worth individuals would look to become venture LPs 14:26 What's the deal with Elizabeth & hippos? Where can you find Jason as his alter-ego "CyberSurfer" 15:49 What is Hustle Fund's portfolio strategy? 18:55 When do you know if you have a 100x outlier? Why roll prior angel investments into the fund? 24:15 Thinking of venture funds from a gambling perspective 28:24 What is Hustle Fund's approach to pro-rata as a smaller fund? 34:49 Founders ability to "game" investors increasing in last 5 years 37:47 How does Elizabeth decide to make the follow-on second bet in a company? 42:01 How does Elizabeth advise her startups to raise from downstream Seed/Series A investors, importance of positive unit economics 47:41 Challenges of fundraising in today's climate 50:34 Reasons for optimism/pessimism, lockdown creating a necessity for innovation 56:55 What will COVID's permanent ramifications be on startups?