Startup Portfolio Highlights

Cindy Bi
4 min readFeb 12, 2020

I published a preliminary analysis of my startup investments via a tweet storm back in December 2019, and here is a quick summary by popular demand.

I’ve invested in more than 100 startups and 8 VC Funds since 2011, mostly via my previous fund and recently with my personal capital.

As of July 2020, I’ve written 16 personal checks within a year, including 9 pre-seeds & seeds, 5 micro funds, and 2 (partial) pro rata from my previous portfolio.

The startups have gone on to raise over $8 billion after my investments and have a total combined valuation of over $60 billion, including 12 unicorns as included in the 25 top startups shown on YC’s top companies list.

Cruise ($30B),

Rippling ($11.25B),

Zapier ($5B),

FlutterWave ($3B),

Retool ($3B),

Algolia ($2.25B),






In the following sections you will find my past portfolio highlights for each vintage organized by year with metrics like: 1) Number of Seeds; 2) Exits; 3) Series A/B/C/D Rounds; 4) Valuation Multiples Since Seed; 5) Notable Mentions.

Vintage — 2011, 2012 and 2013

Vintage — 2014: Unicorn Exit

Vintage — 2015: So Many!

Vintage — 2016: Crazy!

Vintage — 2017: Big Wins Again!

Sabbatical — 2018: More To Share Later

  • Too bad I missed three YC batches: YC W18, YC S18 and YC W19.
  • I may write a separate blog one day to tell my story about that year, which ended up fueling my drive to be dedicated to startup investing full time.

Vintage — 2019: Restart with More Fuel

  • Fully dedicated to VC: again started looking outside of .
  • Made 12 seed investments (66% from YC) within three months.
  • Wrote 6 personal checks including both seeds and pro-rata’s.
  • Series A/B/C: Alpaca, BraveCare, Zippi, Smartex.
  • Started using Twitter actively since July 2019 to have a voice and show how I work in the public.
  • Inbound deal-flow got stronger with very authentic branding.

What’s Next — Hello, CapitalX!

I’ll share more portfolio analysis and insights in the upcoming posts!



Cindy Bi

GP at an enterprise focused generalist investing in 20 startups a year with $100k — $500k checks.