Archangel Gossip Session #2 — Notes

Rayn Ong
3 min readSep 14, 2021

Archangel Ventures organised a casual chat with a few angel investors last Friday. For those who missed out, below is a short summary of our discussion. Thanks to everyone who made it a lively discussion.

What are some of the COVID proof startup opportunities?

  • Ecommerce and logistics are obvious ones but there are challenges to scale in COVID times
  • Smaller players might find difficulty scaling a network due to supply side constraints (eg lack of drivers).
  • Logistics players more generally are under a lot of pressure due to demand spikes from lockdowns.
  • Businesses that support hybrid and remote workforces — eg Remote Social.
  • We discussed Space tech.
  • A lot of hardware focussed companies especially upstream — only starting to adopt start-up tech more recently.
  • Space industry was on hiatus due to COVID providing opportunities for new players.
  • Some emerging players are using existing infrastructure which lends itself to VC investment as there is not prohibitive initial capex in hardware.

YC post demo day valuation discussion

  • Very hot market globally
  • YC post demo day, we see pre-revenue @ $15m — 2nd time founder @ $20m valuation.
  • Also can lead to unfavourable deal terms for investors — eg uncapped SAFEs with no discount.
  • Valuations are running all the way through the curve — seeing consistently secondary deals with ordinary shares worth 150% on the round value within 12 months (in the US). A lot of undisciplined money coming from overseas which is pricing the IPO into the later stage rounds.
  • Discussed AngelList roll up vehicle (RUV) product — no fee no carry service for accredited investors to potentially put in a few thousand dollars each. Can be very useful to bring on strategic investors without having to cut big cheques.
  • Hot deals on syndicated platforms can go super quick even at high valuations — rounds can be filled in 20 minutes.
  • Some companies being actively coached to not provide pro rata
  • YC becoming known as an established place to find winners so increased competition — valuation is all relative — it still can be a great place to find deals given their vetting process potentially does add value especially in challenging geographies.

Best places to find deal flow for certain verticals

  • We talked about places to find quality deal flow for female led startups and facilitated an introduction with Springboard.

The importance of an “accountability buddy” when you angel invest

  • A lot of angels expressed that they do use a buddy or group of friends to keep each other honest and benefit from shared experience.
  • Prevents you from only talking about the winners.
  • Long feedback loop — having someone that you can share the wins and losses over the journey can be very beneficial. Multiple perspectives help you see around corners — helps making decisions not to invest in companies.
  • There are some communities starting to build eg Startmate First Believers — 42 people — weekly/fortnightly master classes — starting to share some deal flow.

Insider rounds — what are they and what do they tell you

  • Generally is one of two opposite signals. eg either a really hot deal rewarding initial investors or an attempt to save the company to bridge to the next phase. Usually it’s the latter and as an insider you will know!
  • Differences between venture funds vs angels — funds make an implicit commitment to see the company through to the end and you will usually follow on unless you’ve really lost faith.
  • Investors may throw a lot of good money after bad to bail failing companies out
  • Can be helpful to clearly set the expectations with the founder before the initial investment, what progress you need to see to justify following-on and investing more.
  • Execution rarely goes to plan — trouble can be an opportunity to be a contrarian and get the best deals. Challenge is spotting what is real trouble vs. “teething issues”.

Thanks to Andrew for the notes.



Rayn Ong

Passionate startup tshirts collector (size M). Ex half-stack developer. Mentor @startmate. LP @blackbirdvc