The Sidekick Small Business Grant for Northern Kentucky/Cincy
If you own a small business in Northern Kentucky or Cincinnati, I don't have to tell you how much you're juggling. You're the owner, the marketer, the bookkeeper, the person who still somehow answers the phone at 7pm. Most days there's no time left over to fix the systems that would actually make all of that easier.
So this fall, I'm doing something about it for two of you!
I'm launching the Sidekick Small Business Grant a brand new program giving away three months of business operations consulting, completely free, to two small businesses right here in Northern Kentucky and the Cincinnati area.
What the Sidekick Small Business Grant Actually Is
Two local small business owners will be selected to receive a fully loaded season of the exact consulting I normally charge clients for, no watered down "sample" version, no strings attached beyond a little goodwill at the end.
I started Sidekick Operations to help small business owners in NKY and Cincinnati move from "doing everything themselves" to actually running their business like a CEO. This grant is a chance to do that for two businesses that might not be in a position to invest in it yet, but need it just as much as anyone.
What Each Winner Gets
I'm awarding two different packages, matched to whatever each winning business actually needs:
One winner receives 3 months of my Scaling Partnership - weekly 60-minute working sessions, custom strategic templates, and hands-on systems design and coaching (a $1,950 value).
The other winner receives 3 months of my Foundational Partnership - one deep-dive 90-minute session a month, with the same templates, async support, and coaching built in (a $1,350 value).
Both come with full ownership of every deliverable we build together and M–F async support by Slack or email, so you're never stuck waiting a week for an answer.
Who This Is For
This grant is built for small business owners based in Northern Kentucky or Greater Cincinnati. To be a good fit, you should:
Own and operate a business that's already up and running (this is about fixing real operations, not writing a business plan from scratch)
Be roughly under $500,000 in annual revenue
Be ready to commit to the session schedule for a full 3 months
Be open to sharing your experience: a testimonial, a review, and being featured as a quick case study once we wrap up
You’ll get value out of this if you’re the only employee and looking to hire eventually or if you have a small team, if you don’t have written processes, if it feels like your workflows are inconsistent and change often, if you have trouble staying organized and productive in your business, or if you feel stuck and need a path for growth.
How Winners Are Picked
I'm reading every single application myself and picking the two businesses that need this most. I'm looking at real operational pain points, whether you're ready to actually do the work, your ties to the NKY/Cincinnati community, and your story.
Applications open September 22 and close October 14, 2026. I'll be reaching out directly to the two winners by October 23, with the partnership kicking off in November.
How to Apply
Apply here. It’s a simple form, just set aside 10-20 minutes to complete it.
If you're a small business owner in Northern Kentucky or Cincinnati who's ready to stop duct taping your operations together, or if you know someone who is, send them this post. Applications close October 14, so don't sit on it!
