Not all donation asks are created equal. If you've ever felt uncomfortable asking a small business to donate product for your community event, trust that instinct. You should feel uncomfortable. Here's a better approach.
Go to the corporations for free stuff. Large corporations have community budgets, marketing budgets and PR incentives built specifically for this. They expect to be asked. Start there. Always.
That said, formal corporate giving programs often require 501(c)(3) nonprofit status and can take time to navigate. A faster and often more accessible approach is going directly to the local store manager. The manager of your neighborhood Starbucks or grocery store frequently has discretionary resources set aside for exactly this kind of community support. They can often say yes to a reasonable ask, some coffee, a few dozen donuts, gift cards for a raffle, without going through a formal approval process. It won't be thousands of dollars worth of product but it doesn't need to be. Ask nicely, be specific about your event and make it easy for them to say yes.
Don't shake down small businesses. Pay them. Full stop. Asking a small business to donate product is asking them to pay their employees, cover their materials and absorb their time in exchange for exposure. Exposure doesn't pay invoices.
Purchase what you need from local small businesses and feature them properly when you do. A sign at the table. Their name in your program. A thank you on your social channels. And reframe how you think about it. This isn't about getting free stuff. It's about creating an opportunity to pour money directly back into your community and help small businesses continue to exist. That's the real win.
For god sakes use your manners. No matter the size of the organization that supported you, corporation or small business, send a thank you letter. Thank them publicly at the event. Use their logo in your materials. Provide any documentation they might need for their records before they have to ask for it. Be a good partner. Create future opportunities. Build relationships that last longer than one event.
Your community events reflect your values. Make sure your asks do too.
