JJ Fliegelman
About JJ Fliegelman
JJ Fliegelman is based in New York. He studied at the University of Pennsylvania, and Tracxn lists a bachelor's degree there in 2011. He is a co-founder of WayUp, a marketplace for employers to recruit college students and recent graduates, which Y Combinator lists as founded by him and Liz Wessel and based in New York City. Tracxn dates his start in the startup ecosystem to 2014 through WayUp. Crunchbase says he received the Forbes 30 Under 30 award.
He has been involved with Y Combinator since 2015. In a LinkedIn post he says he first went through YC himself, stayed in the community for more than seven years, and then spent a year as a Visiting Partner. He writes that in that role he invested in and advised over 120 companies. Crunchbase lists him as a former Visiting Group Partner at Y Combinator.
Since January 2024 Crunchbase lists him as a Partner at First Harmonic. His X profile describes him as building First Harmonic, a former Visiting Partner at YC and a co-founder of WayUp. His LinkedIn headline has described him as a startup founder and investor.
Crunchbase counts 25 personal investments, with no lead investments, no exits and no companies founded. The public Crunchbase profile now shows 26, with Haladir as the most recent listed seed round. Tracxn shows a smaller count of 12 portfolio companies, mainly in enterprise applications and high tech, in the United States and Canada. Counts differ between databases because each tracks a different set of rounds.
His recorded investments are seed rounds, typically alongside institutional funds. Gumloop's July 2024 seed round was led by First Round Capital, and Fliegelman appears among the participating angels. In Reducto's October 2024 seed round, First Round Capital also led, and he appears among the angels. Tracxn lists later seed participation in Double (December 2024), &AI (February 2025), Momentic (March 2025) and Central (August 2025).
On LinkedIn he also writes about running YC Demo Day funds. In a 2024 post he said he was leading his second demo day fund for the W24 batch and had opened it to friends and connections. A later post announces his eleventh YC Demo Day Fund, for the S26 batch.
Crunchbase shows 17 AI investments since 2023 out of 25 in total. The AI companies it lists are Monumint, DryMerge, Martin, Gumloop, Reducto, Outset, Trieve, &AI, Cekura AI, Willow Voice, Brickanta and Central.
Several of these are developer and infrastructure products. Reducto builds document ingestion for large language models and retrieval-augmented generation. Gumloop is a Vancouver-based platform for building AI workflows without code. Trieve provides an API for search, recommendations and RAG. Other recent Crunchbase entries include Haladir, Guide Labs, Laminar, Blacksmith, Mentra and Terminal. This page does not describe those companies because our sources do not say what they do.
The public record shows seed-stage investing, mostly in early YC-linked companies and often next to First Round Capital, General Catalyst, Y Combinator and other funds. Tracxn lists his top sectors as enterprise applications and high tech, with companies in the United States and Canada. Within AI, his investments are mostly in workflow automation, document processing, search and developer tooling.
He has not published a check size, a stated thesis or a list of criteria that we could find. Crunchbase shows no lead investments, so the record is of participating rather than leading rounds. Founders should treat any check size or stage preference as something to ask him directly.
- Reducto: document ingestion for LLMs and RAG. Participated in the October 2024 seed round led by First Round Capital.
- Gumloop: no-code platform for building AI workflows. Participated in the July 2024 seed round, which raised $3.1M.
- Central: payroll, hiring, benefits and compliance for startups. Tracxn records an $8.6M seed round on August 27, 2025.
- &AI: AI company listed on Crunchbase. Tracxn records a $6.5M seed round on February 7, 2025.
- Momentic: Tracxn records a $3.7M seed round on March 4, 2025.
- Double: Tracxn records a $3.9M seed round on December 19, 2024.
- Trieve: API for search, recommendations and RAG. Listed on Crunchbase as an AI investment.
- DryMerge: Crunchbase lists him as an investor in its seed round, which had nine investors.
- Monumint, Martin, Outset, Cekura AI, Willow Voice and Brickanta: listed on Crunchbase as AI investments, with no further detail in our sources.
- crunchbase.com/person/jj-fliegelman
- crunchbase.com/person/05d96ffe-1fe0-f985-5927-b052d75384b4
- linkedin.com/in/jjfliegelman
- linkedin.com/posts/jjfliegelman_demo-day-funds-activity-71632974914366
- x.com/jdotjdotf?lang=en
- tracxn.com/d/people/jj-fliegelman/__rXninT4PZhOj_39Z3sFyOOvJtVwXMI_YTr
- ycombinator.com/companies/wayup
- bctechnology.com/news/2024/7/25/AI-Automation-Startup-Gumloop-Closes-3.cfm)
AI portfolio
Investing activity
JJ Fliegelman has made 25 investments according to Crunchbase. 17 of those investments since 2023 were in AI companies, including Monumint, DryMerge, Martin, Gumloop and Reducto.
Deals
Frequently asked questions about JJ Fliegelman
Who is JJ Fliegelman?
He is a New York-based angel investor and co-founder of WayUp. Crunchbase lists him as a Partner at First Harmonic and a former Visiting Group Partner at Y Combinator.
What AI startups has JJ Fliegelman invested in?
Crunchbase lists 17 AI investments since 2023, including Gumloop, Reducto, Trieve, &AI, Central, DryMerge, Outset and Willow Voice. His investments are mostly seed rounds.
What is JJ Fliegelman's typical check size?
We could not find a check size published by him, so it is not listed here. Ask him directly. Some databases show round sizes, but those are the totals raised by companies, not his own investment.
Does JJ Fliegelman lead rounds?
Crunchbase shows 0 lead investments. His recorded investments are as a participant alongside funds such as First Round Capital.
What stage does JJ Fliegelman invest in?
His recorded investments are seed rounds. He also runs YC Demo Day Funds, which invest in companies from Y Combinator batches.
How can founders contact JJ Fliegelman?
He is on LinkedIn at linkedin.com/in/jjfliegelman and on X as @JdotJdotF. We found no personal website or published pitch instructions.
Is JJ Fliegelman an angel investor?
Yes. JJ Fliegelman invests personally as an angel. Crunchbase counts 25 investments.
What AI companies has JJ Fliegelman invested in?
JJ Fliegelman's AI investments include Monumint, DryMerge, Martin, Gumloop, Reducto, Outset, Trieve and &AI.
Where is JJ Fliegelman based?
JJ Fliegelman is based in New York, United States.
How can founders reach JJ Fliegelman?
Founders on Lounge can see JJ Fliegelman's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add JJ Fliegelman to their Investor Pipeline to track the conversation.