10 Pro Tips & Hot Takes on Angel Investing Today

We recently pulled together 100+ angels…like Reid Hoffman, Chamath Palihapitiya, Elad Gil, Kevin Hartz, Athena Karp, & Nick Caldwell to talk trends and tips in backing entrepreneurs at the earliest stages.

Below are 10 takeaways for how to level up as an angel investor.

“Angel investing is like an open source software project..see how others work, and take and borrow…there’s always a cycling of new ways to look at businesses.” — Kevin Hartz

Screenshots from fireside chats with Reid & Chamath facilitated by Ben Casnocha, and Elad & Kevin facilitated by Erik Torenberg
  1. Take contrarian risks and ask yourself “why would smart people not think this is a good deal? And what do I know that they don’t know?” — Reid Hoffman
  2. Consider these useful indicators of the future: a) Where are the smartest people “dabbling”? b) Don’t try to predict the future… focus on teams rather than future bets. — Ashby Monk, Stanford’s Global Projects Center
  3. Think about SPACs like secondary with liquidity for SPAC holders. You have to really trust the person behind the SPAC and essentially sign away all judgment to them, and you could see a subset of founders much preferring working with a person than the market. — Aadil Mamujee, Musha Ventures & Automattic
  4. Start to build a portfolio and get a feel for investing by allocating your capital across 20 companies with the same quantum to each company because the ability to size is impossible. — Chamath Palihapitiya
  5. Predict if your portfolio is on track by thinking about what the next financing round looks like. Did a smart person lead that financing round? Frequently you won’t have good metrics, you’re making the earlier kind of judgments about people, etc so looking at the next financing round can help condition which things you should be doing. — Reid Hoffman
  6. Don’t think you’re diversifying by investing at different stages because it’s the same risk just more money — Chamath Palihapitiya
  7. Remember it’s active decisioning when you want to put more capital in. As you put more money in a company, you have to think more about it and have a higher probability of being right. — Reid Hoffman
  8. Determine your angel style by considering these 4 components from Elad Gil:
  • What do you invest in: stage, sector, values, team vs. market?
  • How do you help founders, what are your superpowers?
  • How do you get your investments? E.g. networks, referrals etc.
  • What are you known for, what’s your brand? How do you market yourself? what comes up when founders talk about you?

9. Consider going solo capitalist. The shift isn’t just generational but also stylistic in terms of not going for as much percent ownership. e.g. the Notion and Roam rounds where they sold 5% of the company instead of doing a major venture round and selling 20% of the company — Elad Gil

10. Look extra sharp at your next video conference with this pro set up suggested by Tod Sacerdoti, Flex Capital:

  • Sony A5100
  • Dummy Battery for A5100
  • Rode NT-USB Mic
  • Camlink 4k
  • Tripod

Check out the full fireside chat with Reid & Chamath, moderated by Village Partner, Ben Casnocha here:

Here is the fireside chat with Elad & Kevin, moderated by Village Partner, Erik Torenberg:

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