Originally from Akron, Ohio, Ron Nussbaum left the Marines in 2010 and spent the next thirteen years working in residential construction. Along the way, he moved to Emerald Isle and started his first SaaS companies, BuilderComs (which GrepBeat has previously profiled) and Construction Champions.
Four years ago, he met business coach and consultant Rawlings Barnes at an event in New Jersey. After realizing they lived in the same city, they became a tight-knit duo, subsequently meeting every week to discuss obstacles they’d seen businesses encounter. One such obstacle that stood out in particular was the “discrepancy between information and direction for business owners.”
“We live in a time where information is abundant, yet no one has direction,” Nussbaum said. “There is no accountability, and the only way [to bring it about] is spending thousands of dollars on consultants and coaches to try to eliminate that.”
On the back of their consulting expereince, Nussbaum and Barnes thought about creating a more powerful solution for business owners asking “what is the next step?”
In 2025, the co-founders started developing Ask a Shop Owner, an AI-fueled advisor platform built for small business owners that offers on-demand access to expert consulting, with viable solutions to management hurdles.
How AASO works
When creating an AASO account, users complete a quick survey to build their profile, with optional questions about revenue, industry, and employee count. They’ll then begin receiving a daily morning brief consisting of insights tailored to their business and a small goal for the day—which is why the co-founders consider it particularly important to list the industry for one’s business.
“What they list in their profile allows AASO to talk in the right language and use the right background knowledge for those industries,” Nussbaum said. “The more info, the better the information.”
Through the platform’s chat box, a business owner can also ask particular questions, and in return, they’ll receive answers derived from data that is in turn grounded in the experience of actual business owners. Examples of things users might ask about include advice for hiring new leadership, navigating competition, or ways to raise prices without losing the right customers.
Completed steps and milestones, marked with their checklist feature, are saved in the user’s roadmap, located in the sidebar.
The platform is available at a monthly subscription costing $97, but new users can enroll in a seven-day free trial to try it out before signing up to pay.
Setting AASO apart
AASO launched just this past summer and is being built, per its founders, on the principles of experience-first retrieval, conversations, and honest answers.
AASO’s user input resembles generative AI platforms like ChatGPT, but differs because of its limited data sourcing.
With its own data sets, the AI doesn’t gather endless amounts of information from the internet. Rather, it builds solutions from more than 19,000 real-world operator insights, according to Nussbaum. Furthermore, if the platform doesn’t find an appropriate answer at the right moment, it will tell the user rather than generating false information or reaching for something irrelevant.
“We’ve created a frictionless experience by replicating what has worked with other AIs,” Nussbaum said. “And we have completely streamlined it and poured out everything that for your typical business owner just doesn’t work with the other AIs.”
The platform serves 20 industries with more than 254 niches of small businesses. AASO has reached unexpected users as well, with Nussbaum even recalling a local pastor utilizing the platform for his church.
“It’s pretty amazing to see, when you see… a church or a nonprofit start to see value in this…. That right there is more praise than if we just [heard from] people from the industries that we build it for,” Nussbaum said.
QUICK BITS
Startup: Ask A Shop Owner
Co-Founders: Ron Nussbaum, Rawlings Barnes
Founded: 2026
Team size: 2
Location: Wilmington
Website: askashopowner.com
Funding: Bootstrapped
As of now, he and Barnes are continuously testing the platform’s capabilities and working through how their messaging and content as a company should land with potential users. By and large, users appreciate the effort.
“How do we fine-tune things? How do we make things run more efficiently? And how do we convey it in a way that everybody instantly understands it? We are [continuing to] take feedback.”
Within the next year, AASO is planning to expand its team and figure out how to build a bigger community around their product. They aim to establish a “camaraderie” for business owners looking to overcome current hurdles and those who’ve already been there.
“Owners usually aren’t struggling because nobody has ever solved their problem. They’re struggling because they don’t have access to the person who already solved it.”
To learn more about Ask a Shop Owner, visit askashopowner.com.
