AL

Andy Louis-charles

Cohort 10 at Coolwater Capital

Washington DC-Baltimore Area

Overview 

Andy Louis-Charles is a Strategy Executive and Board Director based in the Washington DC-Baltimore Area, with a background in corporate governance, financial analysis, and strategic partnerships. Notable career highlights include serving as Chief Strategy Officer at Custom Ink and founding Wye River Holdings as CEO, demonstrating expertise in business development and corporate strategy. Currently, Andy is actively involved in the investment landscape, serving as a Venture Partner at Hustle Fund and investing in sectors like Real Estate/PropTech and Analytics, showcasing a strong commitment to supporting early-stage companies and fostering entrepreneurial growth.

Work Experience 

CI

Custom Ink

  • Board Advisor

    2024 - Current

  • Chief Strategy Officer (CSO)

    2021 - 2024

  • Senior Vice President Strategy Development

    2017 - 2021

  • Vice President of Business Development

    2011 - 2017

Custom Ink is a provider of an online platform used for custom apparel and accessories for groups and occasions.

Raised $40,750,000.00 from Mark Gillespie, Great Hill Partners, SWaN & Legend Venture Partners and HarbourVest Partners.

customink.com
S

Storyblocks

  • Board Director

    2021

Storyblocks is a subscription service offering unlimited stock media access.

Raised $18,500,000.00 from North Atlantic Capital.

storyblocks.com
H

Hampton

  • Member

    2024

Hampton is a membership community for entrepreneurs, founders, and CEOs.

joinhampton.com
P

Perplexity

  • Business Fellow

    2025

Perplexity is an AI-chat-based conversational search engine that delivers answers to questions using language models.

Raised $165,000,000.00 from IVP, Wayra and SoftBank Vision Fund.

perplexity.ai
WR

Wye River Holdings

  • Founder | Operating Chairman

    2020

    Family Office | Personal HoldCo

SC

Stealth Company

  • Founder | Managing Partner

    2025

    Venture firm under development.

PR

Pressed Roots

  • Investor | Growth Advisor

    2019

Pressed Roots develops a solution for textured hair, making luxury and salon experience available.

Raised $5,046,000.00 from Slauson & Co., RevTech Ventures and Shashi Srikantan.

pressedroots.com
HF

Hustle Fund

  • Venture Partner

    2022

  • Angel Squad | Investor

    2021 - 2022

    Investing with Hustle Fund at https://www.hustlefund.vc/angelsquad

T

Techstars

  • Mentor

    2024

    Techstars Global Mentor

Techstars is an accelerator that provides pre-seed investment and mentoring for various early stage startups.

Raised $108,919,999.00 from SVB Financial Group and Foundry Group.

techstars.com
CC

Coolwater Capital

  • Cohort 10

    2024

    YC for emerging fund managers.

Education 

Articles About Andy

Relevant Websites