WC

Wilson Chockley

Partner at 75 & Sunny

Los Angeles Metropolitan Area

Overview 

Wilson Chockley is a Partner at 75 & Sunny, with a background as an investor at Bain Capital Ventures and experience as an interim CEO at dot.LA. He has a strong track record in venture capital and management roles, with a focus on sectors like Human Capital/HRTech and Real Estate/PropTech. Chockley's career highlights include serving as a Partner at 75 & Sunny, where he leverages his expertise in process improvement and leadership, and his experience as an interim CEO at dot.LA, showcasing his ability to lead and drive growth in dynamic environments.

Work Experience 

  • Partner

    2021 - Current

    Built 75 & Sunny from the ground up with Spencer Rascoff (former CEO/co-founder of Zillow and Hotwire). We've incubated and launched five companies and invested in dozens more.

75 & Sunny is a venture fund and startup studio.

Raised $62,000,000.00 from Steve Salis.

  • Interim CEO

    2023 - 2024

    Took over running dot.LA at a challenging time for the business. Brought it to profitability and sold it in 9 months.

Dot.LA is a digital newsroom covering L.A.'s startup and tech community.

Raised $4,000,000.00 from Jane Park, Brendan Wallace, Todd Jackson, Avery Rosin, Sean Rad, Michael Ryan Dubin, Navid Mahmoodzadegan, CAVU Consumer Partners, Adam Miller and Brian Lee.

  • Investor

    2019 - 2021

Bain Capital Ventures invests in seed to growth-stage startups that uses tech to disrupt existing markets or create entirely new ones.

  • Consultant

    2015 - 2019

  • Category Manager

    2017 - 2018

Thumbtack is a home services website connecting users with local service providers.

Raised $773,200,000.00 from Silicon Valley Bank and Hercules Capital.

  • Analyst

    2014 - 2014

Brown Advisory is an independent investment management and strategic advisory firm.

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