New York Angel Investor Mandate: Matthew on Deals and Diligence
New York City Private Investor Mandate Interview
Founders and capital raisers who want to understand how an attorney-angel evaluates early-stage deals and what he checks in diligence.
Five points worth keeping
- Check size and round stage. Matthew looks for follow-on investments in early-stage rounds. He describes checks of roughly $25,000 to $100,000, both inside and outside the fund.
- Two channels for deals. Cannabis deals go through his own direct investments, since the fund does not invest in cannabis. Tech and consumer goods deals usually run through the fund, which lets him use its resources and colleagues for diligence.
- Following larger funds helps. He likes to piggyback on bigger funds that have done more diligence and help close a round. He says that gives him more confidence the round will fill and the documents are in good shape.
- Three types of companies now. Matthew describes companies already well positioned for the market, companies pivoting their product or message, and companies in distress seeking rescue financing. He says rescue financing is not a fit for him or his resources.
- Fix problems before financing. Matthew says it is much easier to solve problems upfront than on the back end. Time makes issues harder to fix, and a disgruntled party gains leverage when a deal depends on resolving the problem.
Summary
Matthew is an angel investor, a limited partner in a New York City fund, and an active attorney in venture capital and private equity. He also makes direct investments outside the fund, often in cannabis companies, because the fund does not invest in that sector. Tech and consumer goods deals usually go through the fund. In both cases, he describes checks of roughly $25,000 to $100,000, mostly follow-on money in early-stage rounds.
Richard C. Wilson also asks how founders should approach an investor who is a lawyer. Matthew says he is brought onto diligence teams to read documents closely, especially on capitalization, control of IP, and past founder friction. His main advice is to fix problems early. Waiting lets them compound and can give other parties leverage once a financing is underway.
From the source
- Matthew is an angel investor and a limited partner in a New York City fund, plus he makes direct investments outside it.
- His fund is a committed capital follow-on fund, and he describes his checks as roughly $25,000 to $100,000.
- He often sits on a two or three member diligence team that reviews capitalization and control of IP.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: New York City Private Investor Mandate Interview. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.
General education only. Not legal, tax or investment advice.
Talk to a securities attorney to explore options around diligence document review, capitalization table questions and intellectual property ownership. Do not use AI to write your own legal agreements.
In their words
"it's much easier to solve problems upfront than it is to try and fix them on the back end."
"they bring me on because I can look closer at the documents."
"just deal with the problems as they come up and don't let them build up and come to a head in the context of the financing."
Related questions
- How do I close a funding round?I close a funding round by focusing on investors who fit the opportunity and moving each interested prospect through clear, consistent follow-up.
- What documents do investors request during due diligence?Prepare a clear, organized package covering your operations, investments, compensation, team, and track record.
- How do I raise capital for my business?I raise capital by building a repeatable system for attracting the right investors, establishing credibility, and developing relationships before asking for money.
Questions about this video
What check sizes does Matthew invest?
He describes investments of roughly $25,000 to $100,000, usually follow-on money for early-stage rounds. This applies to deals inside the fund and his own direct investments.
What does Matthew look for in diligence as an attorney?
He looks closely at the documents, including capitalization, control of IP, and any founder friction before the deal. He describes wanting to understand the company's background before a deal moves forward.
Which kinds of companies is Matthew less interested in?
He says companies in distress seeking rescue financing are harder for him and his resources. He prefers companies that are well positioned or pivoting toward the current market.
Put this into practice with the data room checklist. See all investor mandates resources.
