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99th percentile
100th percentile
President & CEO of Y Combinator, Initialized Capital founder, Midas Lister
Credibility
Portfolio Scale · 100th percentile
- Made 74+ portfolio investments via Initialized Capital, per Crunchbase.
- Portfolio IPO: Instacart.
- Portfolio IPO: Opendoor (NASDAQ: OPEN).
- Portfolio IPO: Blend Labs (NYSE: BLND).
- Portfolio unicorn (private): Rippling, valued well above $1B.
- Portfolio unicorn (private): Flexport, valued above $1B.
- Portfolio unicorn (private): Patreon, valued above $1B.
- Portfolio acquisition: Cruise Automation acquired by GM (~$1B+).
- Publicly identified as an angel investor (Crunchbase lists him as Individual/Angel Investor).
- Portfolio acquisition: PlanGrid acquired by Autodesk.
- Portfolio acquisition: HelloSign acquired by Dropbox.
- Portfolio acquisition: Bison Trails acquired by Coinbase.
- Portfolio acquisition: Lever acquired by Employ.
Relationship Matrix
Founder score
- 98%Probability of being accurate (98%)Y Combinator S08 alum (Posterous).
- 98%Probability of being accurate (98%)Past co-founder of Posterous (acquired by Twitter) and co-founder of Initialized Capital.
- 98%Probability of being accurate (98%)Notable on Wikipedia as a Canadian-American venture capitalist.
- 95%Probability of being accurate (95%)328,082 LinkedIn followers — broad professional reach.
- 95%Probability of being accurate (95%)ycombinator.com ranks #723 on the Majestic Million (global domain prominence).
- 95%Probability of being accurate (95%)Active on Hacker News with 10,305 karma.
- 95%Probability of being accurate (95%)Current founder of Garry's List and co-founder of Posthaven.
- 95%Probability of being accurate (95%)11 HN posts scored 100+ points (front-paged) — strong community reach.
- 95%Probability of being accurate (95%)Top HN post 'Presumption of stupidity' reached 510 points.
- 95%Probability of being accurate (95%)Fortune 100 Most Powerful People in Business.
- 95%Probability of being accurate (95%)His companies had co-founders (Posterous with Sachin Agarwal, Initialized with Alexis Ohanian).
- 95%Probability of being accurate (95%)Active poster on Hacker News with 52 story posts.
- 95%Probability of being accurate (95%)Identified Hacker News account @garry.
- 90%Probability of being accurate (90%)Top YouTube appearance 'Garry Tan is Out Of Office' has 538,628 views — strong thought-leadership reach (~1.39M total views across 10 videos).
- 90%Probability of being accurate (90%)Wikipedia page averages ~11,792 views/month — widely-known public figure.
- 90%Probability of being accurate (90%)San Francisco Business Times Power 100 honoree.
- 85%Probability of being accurate (85%)Google Knowledge Graph recognizes him as a notable public figure.
- 80%Probability of being accurate (80%)Demonstrates personal technical depth: HN comments cover engineering at Palantir, product/design tradeoffs, and venture math.
- 80%Probability of being accurate (80%)Posterous was acquired by Twitter for approximately $20M.
Investor score
- 98%Probability of being accurate (98%)Portfolio IPO: Coinbase (NASDAQ: COIN).
- 98%Probability of being accurate (98%)Co-founder and Managing Partner of Initialized Capital, a recognized VC firm.
- 98%Probability of being accurate (98%)Forbes Midas List Top 100 Global VC, peaking at #6 globally.
- 95%Probability of being accurate (95%)Made 74+ portfolio investments via Initialized Capital, per Crunchbase.
- 95%Probability of being accurate (95%)Portfolio IPO: Instacart.
- 95%Probability of being accurate (95%)Portfolio unicorn (private): Rippling, valued well above $1B.
- 95%Probability of being accurate (95%)Portfolio unicorn (private): Flexport, valued above $1B.
- 95%Probability of being accurate (95%)Active GP / fund manager — runs Initialized Capital with $3.2B AUM.
- 95%Probability of being accurate (95%)Over 15 years of investing experience since joining YC as a partner in 2010.
- 92%Probability of being accurate (92%)Initialized Capital deployed from $3.2B+ in assets under management.
- 92%Probability of being accurate (92%)Portfolio IPO: Opendoor (NASDAQ: OPEN).
- 92%Probability of being accurate (92%)Portfolio unicorn (private): Patreon, valued above $1B.
- 92%Probability of being accurate (92%)Portfolio acquisition: Cruise Automation acquired by GM (~$1B+).
- 92%Probability of being accurate (92%)Publicly identified as an angel investor (Crunchbase lists him as Individual/Angel Investor).
- 90%Probability of being accurate (90%)Portfolio IPO: Blend Labs (NYSE: BLND).
- 90%Probability of being accurate (90%)Portfolio acquisition: PlanGrid acquired by Autodesk.
- 90%Probability of being accurate (90%)Portfolio acquisition: HelloSign acquired by Dropbox.
- 90%Probability of being accurate (90%)Portfolio acquisition: Bison Trails acquired by Coinbase.
- 85%Probability of being accurate (85%)Portfolio acquisition: Lever acquired by Employ.
What you likely need
You sit at the rare intersection of top-tier accelerator leadership, a $3.2B fund, and your own founding history at Posterous and Posthaven. The most useful Festival events for you right now are small, off-the-record rooms with peer fund leaders, late-stage portfolio CEOs, and politically-engaged SF builders — places to sharpen YC's strategy, scout breakout S26/W26 themes, and connect on your new Garry's List civic work.
Would you attend these IRL Festival events?
We will tune and customize your Founder Festival experience to make sure you get invited to the events that would be most valuable to you.
- tacticalA closed-door dinner with other Midas-List GPs to compare notes on AI-era seed pricing and reserves strategy
- introsA YC alumni founder roundtable with S08–W11 era CEOs to surface lessons for current YC batches
- introsAn Initialized portfolio cohort happy hour with Coinbase, Instacart, Flexport, and Rippling operators for tactical late-stage scaling stories
- positioningAn SF civic-tech builders dinner to develop Garry's List's editorial and community model with fellow politically-engaged founders
- tacticalA designer-founder night for product-led CEOs — drawing on your Palantir/Posterous design-engineer roots
- tacticalAn AI investment thesis workshop with seed GPs to pressure-test what YC should accelerate into in 2026 batches
- introsA Hacker News 'Show HN' creators night to scout under-the-radar technical founders before they apply to YC
- wellbeingA wellbeing offsite for long-tenured tech leaders to share how they sustain energy through public scrutiny and political attacks
