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Richie Chaikof

Principal at Fin Capital

Overview

Richie Chaikof is a Principal at Fin Capital[1], a position Chaikof has held since September 2025[2]. Previously, Chaikof spent nearly five years at Optum Ventures, serving as Principal from December 2020 to August 2025[3] and as Vice President from December 2019 to December 2020[4]. Chaikof's earlier venture capital experience includes work as an Associate at Bain Capital Ventures from February 2017 to December 2019[5]. Before transitioning to venture capital, Chaikof worked in investment banking, including as a Senior Analyst at Citigroup from June 2015 to February 2017[6] and as a Summer Analyst at Barclays in 2014[7]. Chaikof holds an Honors Business Administration degree with distinction from Ivey Business School at Western University, earned between 2011 and 2015[8].

Career history

  1. PrincipalSep 2025 to presentFin Capital
  2. PrincipalDec 2020 to Aug 2025Optum Ventures
  3. Vice PresidentDec 2019 to Dec 2020Optum Ventures
  4. AssociateFeb 2017 to Dec 2019Bain Capital Ventures
  5. Investment Banking Senior AnalystJun 2015 to Feb 2017Citigroup
  6. Investment Banking Summer AnalystJun 2014 to Aug 2014Barclays

Education

  1. Honors Business Administration, With Distinction at Ivey Business School2011 - 2015Western University

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