Zachary Sims
About Zachary Sims
Zach Sims is a co-founder of Codecademy, the online platform for learning to code. He started at Columbia University, and Wikipedia says he dropped out to pursue the venture. He and Ryan Bubinski launched Codecademy in 2011 through Y Combinator's summer program. Before that, he worked at GroupMe, according to Wikipedia. AngelList also lists drop.io and AOL Ventures in his experience.
Codecademy raised a $2.5M Series A in October 2011 and a $10M Series B in June 2012, led by Index Ventures. In a LinkedIn post, Sims said he led the company for 12 years, to more than 50 million learners, and that it had an exit the year before for more than $525M. Codecademy became part of Skillsoft, and Sims then stepped back as CEO. Crunchbase lists his later Skillsoft role as CEO of Codecademy and GM of Technology and Developer.
His X bio describes him as an angel investor, a former Codecademy co-founder and CEO, and "exploring what's next". It lists NYC and SF as his locations. He has also been a Venture Partner at Bowery Capital since 2013, according to NFX Signal.
Crunchbase lists 15 personal investments for Sims. NFX Signal also records 15 investments, and PitchBook lists 21 and classes him as an angel (individual) investor. The counts differ by data source, and none of them is an official portfolio disclosure.
PitchBook's deal list includes Kernel Technologies (October 2025), Cassidy (August 2024) and M3ter (April 2023). Sims has not published a full portfolio list on any page we found.
The AI round on the Lounge deals desk is Eigen's $15M seed in April 2026. Eigen is a San Francisco startup building AI for human connection and collaboration, led by CEO Paul Scherer. Benchmark led the round, according to Eigen's announcement as shared on X. FinSMEs lists Ben Silbermann among the angels. NFX Signal and Crunchbase both list Sims as an investor in the round.
NFX Signal lists Sims as active at pre-seed, seed and Series A. Its sector tags are developer tools, enterprise and consumer internet. It also tags New York City consumer internet seed deals. His own experience is in developer education and software, and his Bowery Capital role covers early-stage software.
NFX Signal gives an investment range of $10K to $250K, with a sweet spot of $100K. That is a third-party profile, not a statement from Sims. We found no public statement from Sims about what he looks for in a pitch.
- Eigen: AI for human connection and collaboration; $15M seed led by Benchmark, April 2026.
- Kernel Technologies: listed by PitchBook as a deal dated October 2025.
- Cassidy: listed by PitchBook as a deal dated August 2024.
- M3ter: listed by PitchBook as a deal dated April 2023.
Investing activity
Zachary Sims appears in 1 AI deal tracked by the Lounge deals desk, rounds totalling $15M. The rounds are mostly Seed, with a median round size of $15M. The most recent is Eigen (Seed, $15M, Apr 2026).
Zachary Sims most often invests alongside Benchmark, Peter Sellis, Terrence Rohan and K5 Global, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Zachary Sims
Who is Zachary Sims?
Zachary (Zach) Sims co-founded Codecademy and led it as CEO for 12 years. He is now an angel investor based in New York, and he is a Venture Partner at Bowery Capital.
What AI startups has Zachary Sims invested in?
The AI round we can confirm is Eigen's $15M seed in April 2026, led by Benchmark. Eigen builds AI for human connection and collaboration.
What is Zachary Sims's check size?
Sims has not stated one publicly. NFX Signal lists a range of $10K to $250K with a $100K sweet spot, but that comes from a third-party profile.
What stages does Zachary Sims invest in?
NFX Signal lists pre-seed, seed and Series A. Its sector tags are developer tools, enterprise and consumer internet.
Is Zachary Sims the same person as other Zachary Sims on LinkedIn?
No. Several people share the name. This page covers the Codecademy co-founder, whose X handle is @zsims and whose site is zacharysims.com.
How can founders reach Zachary Sims?
His public channels are X (@zsims) and LinkedIn. He has not published a pitch process or submission form that we could find.
Is Zachary Sims an angel investor?
Yes. Zachary Sims invests personally as an angel.
What AI companies has Zachary Sims invested in?
Zachary Sims's AI investments include Eigen. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Zachary Sims invest at?
In the rounds tracked on Lounge, Zachary Sims has invested at Seed, with a median round of $15M.
Who does Zachary Sims co-invest with?
Zachary Sims's most frequent co-investors on Lounge are Benchmark (1 deal), Peter Sellis (1 deal), Terrence Rohan (1 deal), K5 Global (1 deal) and Akshay Kothari (1 deal).