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CapitalX

Cindy Bi

cindy@capitalx.vc

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Investor since 2011 -

Top Track Record

Previously: seeded more than 100 startups $7M initial capital is $100M+ (15x).

Deployed ~$40M since Aug 2020 via Rolling Funds and later-stage SPVs

Breakout winners include 25 top YC startups with 15 unicorns Cruise ($30B), Rippling ($11+B), Zapier ($5B), FlutterWave ($3B+), Retool ($3B+), Algolia ($2B+), Go1($2B+), Boom, SendBird, Shipbob, People.ai, Teleport, Cart.com, Turing.com, Owner.com.

1 of 5 startups from 2016 & 2017 vintages (~15x) has become a unicorn.

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Operator & Founder Background

Operated a self-funded & remote-only enterprise software startup for almost a decade with 77 fortune 100 companies as long-time customers.

Bootstrapped and sold a hardware company in 2009 with wholesale & retail distributions across the globe.

Former software consultant @ Accenture; civil engineering PhD Dropout @ Georgia Tech.

Ahead of the “Future of Work” Mainstream Trend for a Decade!

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$2B - $10B+

1. Rippling — Payroll and employee management platform. Valued $13.5B.

2. Zapier — API integration and automation. Valued $5B.

3. FlutterWave (Africa)— Fintech API, Valued $3B+.

4. Retool — Build internal tools remarkably fast. Valued $3.2B.

5. Algolia — Flexible search and discovery hosted API. Valued $2.25B.

6. Turing.com — Unleashing the world's untapped human potential to accelerate AGI. Valued $2B+.

7. Go1 — Enterprise on-line learning platform. Valued 2B+.

$1B — 

7. Cart.com —Leading provider of unified commerce and logistics solutions. Valued $1.2B

8. ShipBob — tech-enabled 3PL that fulfills ecommerce orders for DTC brands. Valued $1B+.

10. Boom Supersonic —  Boomless Supersonic XB-1 Flights, MAKING HISTORY!

11. Teleport — The easiest, most secure way to access infrastructure. Valued $1.1B.

12. SendBird — Chat, voice, and video API. Valued $1B+.

13. People.ai — Revenue Intelligence: AI for Sales and Marketing. Valued $1.1B.

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My Success Getting Into Deals

High conviction & high energy coupled with strategic thinking & critical optimism give me true edge as an empathetic coach and cheerleader for the team.

Founders get inspired by my dedication to seek top talent, devotion to go to bat for their companies and determination to win - they love having me on their cap table!

Winning deals I shared some fun facts on this medium post:from burger dinner, personalized messages, warm intros, matchmaking skill to help founders hire, lightning-fast wires, and sometimes write “love letters” for a very competitive round.

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Evaluation & Investment Process

Data Driven & Remote-First: I collect public data to do thorough research and due diligence to spot anything exceptional for signal of success. I’ve invested in many successful startups without first meeting founders in person since 2011 so my skill set is a perfect fit for this new era of investing and working.

Cohort vs Competitor Analysis: My approach works extremely well for a generalist to pick top 10% startups from a cohort (like YC) that build for the future vs only to perform competitor analysis.

Key Questions & Quick Decisions: I’m well prepared to quickly gauge founder-mission-startup-market fit: invest in the founders and bet on their business.

Enterprise Focused: B2B, FinTech, DeepTech, Education, Healthcare, Automotive, etc.

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Why Cindy @ CapitalX?

Combining an unconventional blend of consultant / founder / operator experience with a decade-long angel investor top track record, I’m well prepared to offer enhanced access and asymmetrical financial returns to LPs via CapitalX.

Investing in startups and operating a self-funded enterprise software company while residing in Silicon Valley and remaining accessible online has honed my analytical insider insight & intuitive outsider mentality for a unique eye for future winners.

There’s also massive opportunity to fuel the existing winners from my past portfolio with expanded LP network and bigger investment amount.

Together, we’ll back more 1% multidisciplinary founders with “chip on shoulder & fire in belly” building hard startups to change the world and bring exponential impact.

To Apply My Decade-Long Craft To Build A Top VC Fund!

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Approach

  • Generalist: enterprise focused, technology driven, mission aligned, invest in founders first.
  • Early & Fast: early enough to be category definer or market leader, with fast execution.

Deal

Flow

  • Founder Network: Past Portfolio Founders, YC and Other Incubators
    • I’ve gained stellar reputation to make quick decisions with high hit rate doing thorough online research and “public data” analysis. Founders love working with me!

  • Twitter @CindyBiSV
    • I’ve built a strong twitter presence since 2019 sharing insights. I often link my tweets in emails to portfolio founders to “write once and share 10x”. Founders appreciate my effort to authentically talk about their products and promote their communities online.

Fund

Admin

  • AngelList Rolling Venture Fund onboarding LPs and deploying capital on quarterly basis.

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Portfolio

Construction

  • Initial Check: $100K - $250K usually, and aim for 1~2% ownership when possible.
  • Sector Agnostic: SaaS, DeepTech, FinTech, Education, HealthCare, Marketplace, etc.
  • Stage: pre-seed, seed, select series A/B for $100m valuation and below.
  • Investments: to deploy $10M+ a year in 30 startups.

Key Terms

  • Management Fee: 2% per annum over each fund's 10-year life, payable quarterly over the first four years.
  • Carry: 20%, increasing to 25% after a 3X return.
  • AL Fee: 0.15% per annum over each fund’s 10-year life, payable quarterly over 10 years.
  • GP Commit: Cindy will reinvest 20% management fees.

Notable LPs

  • 2025 Q3: open to new LPs https://angel.co/v/l/uWNM5

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Select Previous Investments: I

API Integration / Automation

$1M Raised

Seed Only

600x, 2012 Seed

$5B Val. Profitable

Self-driving, Transportation

Acquired by General Motors

38x Exit, 2014 Seed

Unicorn Exit -> $30B

Search APIs: Site, App, Geo

$334M Raised

Series C

180x, 2014 Seed

$2.25B Valuation

Smart Bottleless Water Dispensers

$130M Raised

Series D

100x, 2014 Seed

Logistics (E-commerce)

$330M Raised

Series C

100x, 2015 Seed

Unicorn

Consumer Electronics,

Sleep Wellness

$70M Raised

Series C

30x, 2015 Seed

Valuation Multiples Since Investment*

Follow-on Investors & Total Funding

* close estimates without considering any dilution.

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Select Previous Investments: II

Education, E-Learning,

Corporate Training

$84M Raised

Series C

50x, 2015 Seed

$2B Valuation

Cloud Infrastructure

$59M Raised

Series B

100x, 2015 Seed

Unicorn

Chat APIs - Text, Audio, Video

$121M Raised

Series B

70x, 2016 Seed

Unicorn

Enterprise Software,

A.I., Machine Learning

$100M Raised

Series C

100x, 2016 Seed

Unicorn

Fintech: Payment APIs

$47M Raised

Series D

300x, 2016 Seed

$3.2B Valuation

Aerospace, Transportation

$245M Raised

Series C

50x, 2016 Seed

Unicorn

* close estimates without considering any dilution.

Valuation Multiples Since Investment*

Follow-on Investors & Total Funding

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Select Previous Investments: III

Hardware, Mobile Identity,

Touchless Workplace

$59M Raised

Series B

25x, 2016 Seed

SaaS, Cloud Infrastructure,

Continuous Delivery

$82M Raised

Series C

10x, 2017 Seed

SaaS, Mobile CMMS

$49M Raised

Series B

35x, 2017 Seed

SaaS, Employee Management,

HR & IT

$700M Raised

Series D

SPV, 2017 Seed

$11B Valuation

Education, E-Learning,

ISA

$122M Raised

Series C

20x, 2017 Seed

Enterprise Software,

Productivity Tools

$141M Raised

Series C

250x, 2017 Seed

$3B Valuation

* close estimates without considering any dilution.

Valuation Multiples Since Investment*

Follow-on Investors & Total Funding

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Questions? Let’s Talk!