Monticelloam
About Monticelloam
Monticelloam, LLC was founded in October 2014 by Alan Litt, Thomas Lally and Jonathan Litt, according to the firm's January 2025 press release. It is based in New York and describes itself as a specialized multifamily and seniors housing lending platform. It offers bridge, working capital and permanent financing across the U.S. The firm also runs an advisory practice covering loan workouts, restructuring and servicing. LinkedIn lists it as privately held with 11 to 50 employees. In 2021 it announced a joint venture with Greystone for healthcare capital solutions. Crunchbase and Caplight list Alan Litt, Jonathan Litt and Tom Lally as founders or principals. Monticelloam is not a venture capital firm. No dedicated AI investing team or AI partner is named in public sources.
Monticelloam's AI exposure comes from one deal, and it is tied to its lending business. Hypha is an AI-native platform that structures documents and data for underwriting, portfolio monitoring and asset management. Monticelloam worked with Hypha from the start as a design partner, helping shape the product around real underwriting and asset management workflows. It then took part in Hypha's seed round. Alan Litt, a principal, co-founder and board member of Monticelloam, said in the announcement that Hypha embeds the firm's institutional knowledge into the platform. Several other investors in the round were also customers or design partners. Caplight records Monticelloam as a co-investor, not a lead, and shows two Hypha entries dated June 2026. These are the same round listed twice. Founders should read this as a strategic investment by an operator in a sector it knows. It does not show a standing AI fund.
Monticelloam's only recorded AI investment is a seed round, which Hypha announced on June 11, 2026. Its own check size in that round is not public. Public sources give no stated stage focus, check size range or dedicated venture fund for AI. PitchBook lists a real estate debt fund called Monticello Capital Partners, vintage 2021, managed by Monticelloam. Its size is not shown publicly, and it is not an AI vehicle. The firm's published deal sizes are loans. Examples are a $22M working capital facility and a $400M bridge financing for skilled nursing facilities, both announced in early 2025.
- Hypha: AI-native asset intelligence platform for private credit, private equity, real estate and healthcare investors. It was founded in 2025 by Peter Wang and Simcha Hyman and is based in New York. It raised a $50M seed round in June 2026, led by TriEdge Investments, with Monticelloam participating.
- monticelloam.com/about
- monticelloam.com/monticelloam-funds-22-m-working-capital-facility-for-
- pulse2.com/hypha-raises-50-million-seed-round-as-it-emerges-from-steal
- proptechconnect.com/hypha-announces-a-50m-seed-round
- caplight.com/investor/monticelloam
- pitchbook.com/profiles/fund/17829-01F
- globenewswire.com/news-release/2021/05/24/2234803/30865/en/Greystone-a
- linkedin.com/company/monticelloam
Investing activity
Monticelloam appears in 2 AI deals tracked by the Lounge deals desk, rounds totalling $100M. The rounds are mostly Seed, with a median round size of $50M. The most recent are Hypha (Seed, $50M, Jun 2026) and Hypha AI (Seed, $50M, Jun 2026).
Monticelloam most often invests alongside TriEdge Investments, CFG Bank, Dwight Capital and Crescent Heights, and the companies it backs on Lounge are mostly in AI.
Deals
Frequently asked questions about Monticelloam
Is Monticelloam a venture capital firm?
No. Monticelloam describes itself as a specialized lender for multifamily and seniors housing, with advisory and servicing services. Its one known AI investment is Hypha, a company that worked with it as a design partner.
What AI companies has Monticelloam invested in?
The only public AI investment is Hypha, which raised a $50M seed round in June 2026. TriEdge Investments led the round and Monticelloam took part as a co-investor.
Who leads AI investing at Monticelloam?
No AI investing lead is named publicly. Alan Litt, a co-founder and principal, was quoted in the Hypha announcement. Jonathan Litt and Tom Lally are listed as other principals.
What check size does Monticelloam write for AI startups?
It has not published a check size or a stage range. Its share of the Hypha seed round was not disclosed.
Does Monticelloam invest in AI startups outside real estate and healthcare finance?
No public evidence of that exists. Its single known AI investment, Hypha, serves sectors close to its own lending, namely senior housing, healthcare and multifamily real estate. Founders in those areas are the most likely fit.
What stage does Monticelloam invest at?
In the rounds tracked on Lounge, Monticelloam has invested at Seed, with a median round of $50M.
Who does Monticelloam co-invest with?
Monticelloam's most frequent co-investors on Lounge are TriEdge Investments (2 deals), CFG Bank (2 deals), Dwight Capital (2 deals), Crescent Heights (2 deals) and Yakar Partners (2 deals).
How can founders reach Monticelloam?
Founders on Lounge can see Monticelloam's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with the firm under Warm Paths, and add Monticelloam to their Investor Pipeline to track the conversation.