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 $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),

Go1($2B),

Boom,

SendBird,

Shipbob,

People.ai,

Teleport.

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

• Take it slow and learn: 13 startups and 1 VC Fund.
• Outlier Winner: Zapier, single pick from YC S12. 600x at $5B valuation.
• Exits: Mailgun, Meldium, SimpleLegal and Semantics3.
• Series A/B: LeadGenius, MyVR, Trusper/Musely, Strikingly.
• 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, now valued at $30B), FrontLeaf, Chewse, and Epic!,
• Other Unicorn: Algolia valued at $2.25B.
• Series A/B/C: Bevi, Sense.ly, MTailor, NextCaller.
• Multiples: 190x, 50x, 40x, 30x and 20x etc.
• March 2014 — breakout 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 /D (publicly announced): BitMovin, EightSleep, Flirtey, Go1, Gravitational, Jopwell, PaperSpace, PickTrace, ReadMe, ShipBob, PlateJoy, etc.
• Multiples (40% of 35 investments): 100x, 40x, 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).
• Breakout Winners: Go1 ($2B), Shipbob unicorn, Teleport unicorn.

Vintage — 2016: Crazy!

• Unbelievable number of breakout winners: 26 seed investments with 4 unicorns.
• Exit: Innov8.Work (India).
• Series A/B/C/D (publicly announced): Boom Supersonic, SendBird, People.ai, FlutterWave, Proxy, DeepGram, PetCube, Wallarm, Drivezy.
• Multiples: 300x, 100x, 80x, 50x, 40x, 30x, 25x, 20x, 10x etc.
• Investments in India and Africa: Innov8.Work, Drivezy, FlutterWave.
• Breakout Winners: Flutterwave ($3B); Unicorns - Boom, SendBird, People.ai.
• * 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. It has proved to work well and I directly invested in 25 top 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/C/D: UpKeep, Rippling, LambdaSchool, Retool, Armory, Pyka, Snappr, GetJerry, MinoMonsters etc.
• Multiples: 250x, b100x, 60x, 15x, 10x, 5x, etc.
• Seed Valuations: $6m, $8m, $10m, $12m, $15m, $20m, $25m and uncapped with discount.
• Breakout Winners: Rippling ($11.25B), Retool ($3B), etc.

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.
• 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!