/Companies

StackSource

AcquiredTechstars '16

New York City, US · Founded 2015 · 6 employees on LinkedIn · 1 known investors

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StackSource operates a digital marketplace and matching platform for commercial real estate financing, connecting borrowers and brokers with lenders through algorithmic deal posting and real-time capital market data.

Also known as StackSource

Founders & leadership

NWNathan Wall
Nathan WallCTO

Investors · 1

Techstarslisted by TechstarsBoulder · $220K

How we know: the Techstars portfolio · open dataset · Top 3000 Accelerator Startups (no YC) 2026-08 · Not right? Tell us

Company profile

researched Sep 2026

StackSource is a New York City-headquartered commercial real estate capital markets platform that connects borrowers, brokers and investors with lenders for commercial mortgage financing. The platform tracks the loan programs of hundreds of active lenders and lets a user post a deal once, after which an algorithm notifies only lenders whose stated criteria — geography, asset type, loan size and other variables — match the deal. Lenders define their lending parameters and receive filtered, structured deal submissions; investors and brokers receive real-time feedback, questions and offers from verified lenders.

Alongside matching, StackSource provides a data layer built from its pool of loan quote and transaction data, including daily rate updates across lender types and loan products, lender behavior trends, rate benchmarks and recent-deal tracking surfaced in a user dashboard. Historically the company paired the technology platform with human Capital Advisors who guided borrowers from submission to close, on the basis that commercial mortgages are not as commoditized as residential loans. Earlier product work included a free Chrome browser extension that applied StackSource loan quote data to commercial property listings across the web so investors could analyze acquisition opportunities.

In April 2024, Commercial Observer reported that StackSource, after struggling financially in a turbulent CRE credit market, entered a merger and acquisition agreement with Los Angeles-based Max Benjamin Partners, with no payout to holders of common equity, including the employee stock pool, and with founder equity also wiped out. The stacksource.com marketplace remains online, presented as a lending marketplace in free early access with a 2025 copyright notice.

Founding story

Co-founder and CEO Tim Milazzo was exposed to commercial real estate through his father, a commercial real estate broker in New York City. He studied finance in college and interned at a large real estate firm, then worked in advertising technology at Google and later Facebook before returning to commercial real estate, seeing an opportunity for online technology to help investors find the best financing for a property without tracking hundreds of lenders' programs themselves.

Business model

StackSource operates a two-sided marketplace between commercial real estate capital seekers (investors, developers, brokers) and lenders, layering market data and advisory services on top of lender matching. Historically it functioned as a commercial mortgage advisory/brokerage arranging financing deals for property investors, supported by a fleet of experienced Capital Advisors who worked deals from submission to close.

The current platform is advertised as 100 percent free during early access. The company previously operated a commercial mortgage financing/advisory service in which Capital Advisors arranged loans for borrowers.

Traction

The company reported doubling its market share in 2020 and had closed approximately $1 billion in financing deals in about three years as of August 2022. Named transactions include $60.8 million of acquisition financing for Impex Capital Group and Bridge Investment Group's purchase of The Harmony Apartments in Arlington, Texas, and $32.6 million of construction financing for GoodNeighbor Properties for a mixed-use property in Alexandria, Minnesota.

Latest developments

In April 2024 StackSource entered a merger and acquisition agreement with Los Angeles-based Max Benjamin Partners after an investment offer fell through, several capital advisers departed and attempts to secure bridge funding failed; the deal produced no payout for common shareholders, the employee stock pool or founders. The stacksource.com marketplace continues to be offered to brokers, lenders and investors free of charge during an early-access period, carrying a 2025 copyright.

▸Full profile — market position, technology, go-to-market, geography, history, risks & controversies

Market position

StackSource positions itself against traditional commercial mortgage brokerage, which its CEO characterized as a local, relationship-driven business, by arguing that commercial real estate is also an information business in which data can extend reach beyond local relationships. It describes itself as the only commercial mortgage platform offering daily rate updates across lender types and loan products.

Differentiators cited by the company include a self-improving lender-matching algorithm, exclusive lending data drawn from thousands of real estate transactions, daily rate and trend updates, real-time feedback from verified lenders, and the pairing of an online platform with experienced human Capital Advisors rather than a fully automated process.

Technology

The platform combines real-time deal posting with an algorithmic lender-matching engine that filters notifications by lender criteria and refines its matching and recommendations as more deals are posted. It maintains a database of loan programs from hundreds of active lenders and a proprietary pool of loan quote and transaction data used to generate daily rate updates, rate benchmarks and lender performance metrics. Earlier tooling included automated instant soft quotes for qualified properties and a free Chrome extension that overlaid financing quotes onto commercial property listings found on the web.

Go-to-market

Commercial real estate investors, developers and owners seeking debt; commercial mortgage brokers sourcing lenders; and banks and other lenders seeking qualified, criteria-matched deal flow. Its deal activity has centered on property types including suburban office, multifamily, construction and mixed-use assets.

Geography

Headquartered in New York City with nationwide U.S. deal activity, including arranged transactions in Arlington, Texas and Alexandria, Minnesota, and a focus on suburban office and multifamily markets across the country. The company operated with a remote workforce.

History

Founded in 2015 and headquartered in New York City, StackSource spent several years delivering financing quotes to real estate investor clients. It said it doubled its market share in 2020 as investors sought financing answers during the pandemic while some local banks pulled back, and it closed its first formal fundraising round in the second quarter of 2021. It appointed commercial real estate veteran Richard Caldwell as EVP, Head of Originations around 2021. By August 2022 it had closed roughly $1 billion in financing deals over about three years. In April 2024 it agreed to merge with Los Angeles-based Max Benjamin Partners after failing to secure bridge funding, with investor and founder equity wiped out; Milazzo subsequently listed himself as a consultant to Max Benjamin Partners.

Risks & controversies

StackSource struggled financially amid a turbulent commercial real estate credit market, lost capital advisers and saw an investment offer fall through. Its 2024 merger with Max Benjamin Partners left holders of common equity shares, employee stock options, adviser shares and founders with no value. CEO Tim Milazzo cited market timing, unproductive executive hires and difficulty maintaining a cohesive culture in a remote environment as contributing challenges.

Compiled by commissioned research from 5 cited public sources — announcements, filings, and press listed under research sources below.

Key figures

latest reported
Cumulative financing deals closedAug 2022$1B
HeadcountAug 20266

Company-reported or press-reported figures, each dated to when it was claimed — not independently audited.

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Timeline · 6

launches, deals, and filings
Apr 2024
Merger and acquisition agreement with Max Benjamin Partners

Los Angeles-based Max Benjamin Partners entered into a merger and acquisition agreement with StackSource. The deal was not sufficient to pay out holders of common equity shares, including the employee stock pool, and founder equity was also wiped out. CEO Tim Milazzo subsequently listed himself as a consultant for Max Benjamin Partners.

source ↗

Oct 2022
Arranged $60.8M acquisition financing for The Harmony Apartments

StackSource arranged $60.8 million of acquisition financing for Impex Capital Group and Bridge Investment Group to buy The Harmony Apartments in Arlington, Texas.

$60.8M source ↗

Jun 2022
Arranged $32.6M construction loan in Alexandria, Minnesota

StackSource arranged $32.6 million in construction financing for GoodNeighbor Properties for a mixed-use property in Alexandria, Minnesota.

$32.6M source ↗

Jan 2021
First fundraising round closed in Q2 2021

CEO Tim Milazzo said the company raised its first proper fundraising round in the second quarter of 2021 to advance automation of the commercial mortgage origination process; amount and investors were not stated.

source ↗

Jan 2021
Richard Caldwell appointed EVP, Head of Originations

StackSource appointed commercial real estate industry veteran Richard Caldwell as EVP - Head of Originations.

source ↗

Jan 2021
Chrome browser extension for financing quotes

StackSource launched a free Chrome browser extension that applies its loan quote data to commercial property listings across the web so investors can analyze potential acquisition opportunities.

source ↗

Dated company events from announcements, filings, and press; legal rows summarize public dockets and regulator releases.

In the news

▸Research sources · 5

primary sources listed

5 public sources were cited for this profile; the first-party ones are listed here.

Frequently asked questions

What does StackSource do?
StackSource is a commercial real estate lending marketplace that matches borrowers and brokers with lenders using deal data and algorithms.
Who are StackSource's investors?
StackSource's investors include Techstars.
Where is StackSource headquartered?
StackSource is headquartered in New York City, US.