Cort Gross is a community finance and development consultant, and the founder and principal of Wessington Ventures, LLC. Mr. Gross focuses his efforts within two broad areas of expertise—community investment and the financing and development of community controlled real estate. Mr. Gross brings over 20 years experience in the field, working for more than ten years as a consultant, and, before that, as CFO of nonprofit housing developer BRIDGE Housing Corporation, Vice President of Affordable Housing with mortgage banker TRI Capital Corporation (now known as PNC Mortgage), and as Program Manager for Lending with community development financial intermediary the Low Income Housing Fund (now known as LIIF). He has served on several nonprofit boards and finance committees and published occasional articles. He currently sits on regional and national loan committees for the Nonprofit Finance Fund, and the finance committee of the northern California chapter of the Green Building Council. A former Coro Fellow in public affairs, Mr. Gross received his A.B. degree in history at Stanford University and his M.Div. Degree in liberation theology at Yale University.

Facilitating community development capacity has been constant in Wessington’s work. We have worked with a wide array of community-based and nonprofit organizations on a large and diverse range of projects, building organizational capacities as well as homes and commercial space. Our principles and skills are detailed below.


Mission. Wessington is dedicated to accessing and leveraging capital for community asset building. Wessington does community development.

Impact. Wessington focuses explicitly on development approaches and investment strategies that can achieve sustainable impact.

Client primacy. Wessington does what its clients need, not simply what financial products might call for. We are always leery of falling in to the professional trap summed up by a favorite aphorism: when you only have a hammer, every problem looks like a nail.

Partnership. As Wessington responds to its clients to meet their needs, we also recognize limitations. Good service often calls for collaboration or referral as a consequence. Wessington strives to provide the best response to the need, and the highest level of creativity in problem solving.

Integrity. Wessington deeply values honesty, fairness, and transparency in all its work. We endeavor—we venture—for it daily.

Project management

We are experienced in overall real estate project management, from concept to completion. We can define and manage the big picture and sweat the little details. At the client's direction, we can assist on real estate projects in the selection of consultants, appraisers, architects, attorneys, market analysts, general contractors, and other project personnel, advising on their hiring and then managing them through to completion of the contemplated task. We can secure and review environmental reports, evaluate property management and business plans, obtain grants from foundations and units of government, purchase land for development or inventory for production, and analyze partnership agreements, leases, and operating proformas. We can function as the owner's representative during construction or rehabilitation of real estate. We are adept at negotiating the entitlement process in several localities.

Program development

We have played an active role in the formation and management of several community development financial institutions (CDFls) and nonprofit housing development corporations (HDCs), developing various cash management, portfolio management, and development programs, as well as underwriting and credit administration infrastructures, drawing on our deep experience developing such procedures as senior staff with the Low Income Investment Fund, one of the nation's leading CDFls, and BRIDGE, one of its leading nonprofit housing developers. We have also advised local governments on administration of various federal and state funding programs, especially as it reflects best practices for community development finance.

Organizational Development

As Wessington has advised on program or project development, we find we are often working on organizational development. While we do not profess particular expertise in board formation, strategic planning or other typical management consulting concentrations, we have found that the ability to express an opinion on these matters can be helpful, especially as the formation and consequent management of separate entities is required for a development or financing project. As we have worked to craft capitalization strategies with clients, for instance, we find that many of the same techniques of, say, identifying stakeholders or articulating a theory of change, that inform management consulting can also supplement our more typically task specific work. We work to stay informed of the latest thinking in nonprofit management as a consequence.

Feasibility analysis

Wessington can provide speedy and thorough assessments of actual or proposed real estate projects or financing structures. Cort Gross has served as an expert in legal proceedings, and has provided numerous feasibility analyses, from the "quick and dirty" to the comprehensive, reviewing the work of others or generating new analysis based on an informed investigation of conditions for real estate markets, the capital markets, or both.

Project financing

We have applied our lending experience in our development work, structuring, applying for, and securing predevelopment and feasibility, land acquisition and site development, construction, permanent, and gap financing for our clients, and making use of a variety of innovative tools such as loan guaranties, interest rate write downs, and tax advantaged loan or investment structures on projects for which we have consulted, in particular those using Low Income Housing Tax Credits (LIHTC) and New Markets Tax Credits (NMTC). Over the past 20 years, Cort Gross has personally closed hundreds of financings, ranging from a few thousand dollars to tens of millions of dollars. As a loan committee member, a senior manager, or as staff reporting to a credit committee, he has overseen the underwriting and structuring of many more loans and investments.


Our experience has been very practical in the sense that it makes for good training—not the kind where a consultant brings in a one size fits all Power Point deck and charges the nonprofit a lot of money for a report that will sit on the shelf. Wessington does structured, unique trainings on specific issues.We have consequently found that our trainings often end up as something other—either more or less—than initially requested. Our approach involves asking a lot of questions, and we find that a client often discovers their need is not what they first envisioned. We do our best to respond to it. Wessington is well positioned to provide organizational and technical training to local governments, to community based or larger non-profits, and to resident organizations seeking to manage a government financing program, to lend, to borrow, to start a business or to acquire or develop real estate.