Startup Portfolio Highlights

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 $7 billion after my investments and have a total combined valuation of over $30 billion, including 3 unicorns (Cruise, Zapier and Rippling), and 10 future unicorns like Algolia, SendBird, Rippling, FlutterWave, People.ai, UpKeep, Boom Supersonic, Proxy, ShipBob, LambdaSchool, Retool, etc. as shown on YC’s top companies list.

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 Rounds; 4) Multiples: Approximate Valuation Markups Since Seed; 5) Notable Mentions.

Vintage — 2011, 2012 and 2013

• Take it slow and learn: 13 startups and 1 VC Fund.
• Outlier Winner: Zapier, single pick from YC S12. 500x IF you ask me!
• Exits: Mailgun, Meldium and SimpleLegal.
• Series A/B: LeadGenius, MyVR, Trusper/Musely, Strikingly, Semantics3.
• Misses (2012): Gusto and Intercom — committed to invest and even got term sheet for Intercom, but didn’t close the deals due to lack of experience and high conviction.

Vintage — 2014: Unicorn Exit

• Big quantity with a lot more to learn: 32 seed investments.
• Exits: Cruise (unicorn exit within 18 months) and FrontLeaf.
• Series A/B/C: Algolia, Bevi, Chewse, Epic!, Sense.ly, MTailor, NextCaller.
• Multiples: 50x, 40x, 30x and 20x etc.
• March 2014 — huge success with winners like Cruise and Algolia.
• August 2014 — notable winners like Bevi and Epic!

Vintage — 2015: So Many!

• More capital deployment: 35 seed investments and 2 VC Funds;
• Exits: Interviewed and Auro.ai.
• Series A/B/C (publicly announced): BitMovin, EightSleep, Flirtey, Go1, Gravitational, Jopwell, PaperSpace, PickTrace, ReadMe, ShipBob, PlateJoy, etc.
• Multiples (40% of 35 investments): 30x, 20x, 10x, 5x, 3x, 2x etc.
• Seed Valuations: $5m, $8m, $10m, $12m, $15m, $30m and uncapped.
• Investment in LATAM: Platzi (Mexico first and later Brazil).

Vintage — 2016: Crazy!

• Unbelievable number of breakout winners: 26 seed investments with 5 of them got listed on Y Combinator’s top 101 startups*.
• Exit: Innov8.Work (India).
• Series A/B/C (publicly announced): Boom Supersonic, SendBird, People.ai, FlutterWave, Proxy, DeepGram, PetCube, Wallarm, Drivezy.
• Multiples: 50x, 40x, 30x, 25x, 20x, 10x etc.
• Investments in India and Africa: Innov8.Work, Drivezy, FlutterWave.
• * I’ve decided to focus on Y Combinator for seed investments since 2016 for best use of my time because I was a full-time operator at Aspose. It has proved to work well and I directly invested in 11 of the top 101 YC startups.

Vintage — 2017: Big Wins Again!

• Breakout Winners: 23 investments and 9+ raised follow-on rounds;
• Quick Exits: Scaphold and GetPyApp.
• Series A/B: UpKeep, Rippling, LambdaSchool, Retool, Armory, Pyka, Snappr, GetJerry, MinoMonsters etc.
• Multiples: 40x, 15x, 10x, 5x, etc.
• Seed Valuations: $6m, $8m, $10m, $12m, $15m, $20m, $25m and uncapped with discount.

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 Y Combinator.
• Made 12 seed investments (66% from YC) within three months.
• Wrote 6 personal checks including both seeds and pro-rata’s.
• 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!