If I won a Boss Up competition in the past, can I re-apply?

No. Past winners are not eligible to apply again.

Who is eligible to apply?

Entrepreneurs who are authorized public housing (NYCHA) or NYCHA Section 8 residents in “good standing” (listed on the lease and current on rent) and who are at least 18 years of age as of May 1, 2025. “Good Standing” defined as compliant with NYCHA lease, including the obligation to be current in rent, regardless of whether you have applied for and/or received any form of emergency rental assistance.

What if English is not my first language?

The application, pitch presentation, and classes will only be offered in English. However, if you know someone who can help translate for you, you may participate with their support.

What supporting documents do I need to provide?

Entrepreneurs selected to present their businesses in a pitch competition will be required to submit proof of business ownership (one of the following): business certificate, NYS incorporation documents, tax statement or bank statement.

What is the award and how is it structured?

The selected winners will receive a grant of $20,000 paid in 2 installments:

• $5,000 upon selection

• $15,000 upon completion of a training program offered in fall 2025

What are the IRS/tax implications of the award?

The winners will be required to complete a W9 Form and they will receive a 1099 at the end of the year and the grant will be reported to the IRS and New York State. 

Entrepreneurs should speak with a tax professional about the tax implications of the $20,000 grant if they are selected as a winner.

Will NYCHA count the grant as income?

According to NYCHA, because the grant is not a recurring payment, the $20,000 will not be counted as income. You can confirm this with your housing assistant or with the Leased Housing Department.

How can I stand out in my application?

The judges panel will be paying close attention to what an entrepreneur plans to do with the grant. In the application, be as specific as possible. Sharing a budget of where the money will be used can make a strong case. If you have marketing materials and want the grant for advertising, show what you have created and how much it will cost to distribute. There is space to upload additional materials that will inform the judges about the current business and projections for future growth.

If I won a Boss Up competition in the past, can I re-apply?

No. Past winners are not eligible to apply again.

How does Boss Up define Veteran?

The NYC Charter, Chapter 75, Section 3101 defines Veteran as a person who serves/has served in the active military service, including navy, Coast Guard, air force, marines, army, space force, and their respective national guard or reserve components, regardless of discharge status or time served. Veteran also means a person who serves/has served in the US public health service, or a commissioned member of the oceanic and atmospheric administration. 

Veterans will need to show a DD-214 or Veteran ID.

What is needed to show proof of being a member of a Gold Star Family?

Copies of military orders, discharge paperwork, or other indicators of the service member’s status immediately before death; copies of any official record of the last known address and other contact information; copies of other official documentation such as death certificates, marriage licenses; and social security information.

How does Boss Up define “military spouse”?

Any individual who is legally married to an individual who is a member or was a member of uniformed service. People entering the pitch competition must show a marriage license.

What if English is not my first language?

The application, pitch presentation, and classes will only be offered in English. However, if you know someone who can help translate for you, you may participate with their support.

What supporting documents do I need to provide?

In addition to the documentation listed above for veterans, Gold Star families and military spouses, entrepreneurs selected to present their businesses in a pitch competition will be required to submit:

• Proof of business ownership (one of the following): business certificate, NYS incorporation documents, tax statement or bank statement.

How can I get a copy of my DD-214?

To request a copy of your DD-214, contact the National Archives.   If you have any questions about or need assistance in locating your DD-214, please contact DVS at connect@veterans.nyc.org or 212-416-5250.

What is the award and how is it structured?

The selected winners will receive a grant of $20,000 paid in 2 installments:

• $5,000 upon selection

• $15,000 upon completion of a training program

What are the IRS/tax implications of the award?

The winners will be required to complete a W9 Form and the grant will be reported to the IRS and New York State. 

Entrepreneurs should speak with a tax professional about the tax implications of the $20,000 grant if they are selected as a winner.

How can I stand out in my application?

The judges panel will be paying close attention to what an entrepreneur plans to do with the grant. In the application, be as specific as possible. Sharing a budget of where the money will be used can make a strong case. If you have marketing materials and want the grant for advertising, show what you have created and how much it will cost to distribute. There is space to upload additional materials that will inform the judges about the current business and projections for future growth.