Nov 1, 2025
From Corporate Finance to Coffee Shops: How AI is Reshaping Small Business Operations
Isaac's story isn't unusual for entrepreneurs. He left a stable finance career in New York, bought his first rental property, and eventually built a thriving property management company with his wife. Then, because managing dozens of properties wasn't enough, they opened Screaming Cat Ice Cream and Coffee six months ago.
What makes Isaac's journey relevant in 2024 isn't just the hustle—it's how he's navigating the intersection of traditional business operations and emerging AI technology. And more importantly, where he's leaving opportunities on the table that other small business owners can learn from.
The Corporate-to-Entrepreneur Leap
Isaac spent years in client-facing finance roles, creating portfolio presentations and managing client relationships. When he and his wife started purchasing rental properties in Jacksonville in 2018, they quickly realized the systems and processes from corporate finance translated perfectly to property management.
"We wanted to set the standard really high and treat people's investment properties the same way financial advisors treat portfolios," Isaac explained. "It's about keeping it at a fairly high standard."
That mindset—treating a small business with corporate-level rigor—became their competitive advantage. They didn't just manage properties; they built systems, tracked metrics, and created playbooks that could scale. By 2020, they had officially left their jobs and relocated to Jacksonville full-time.
The turning point? When Isaac calculated that managing 50, 100, or 500 properties at standard fees could outpace his corporate salary. The potential for unlimited growth beat the security of a capped paycheck.
The AI Awakening: Starting Small, Thinking Big
Here's where it gets interesting for today's small business owners. Isaac is using AI, but he's honest about where he is in the journey—and that honesty is refreshing.
Current AI Applications:
Isaac's team uses AI for three primary functions right now:
Content ideation for social media - Not copy-pasting AI-generated captions, but using it to brainstorm angles and themes, then adding their personal touch
Legal document analysis - When an HOA demanded tenant lease information citing their bylaws, Isaac fed the hundred-page document into AI and asked it to find the specific clause. It didn't exist. Instead of spending days reading legal jargon, he had his answer in minutes.
General research and exploration - Running ideas past AI to get different perspectives before making decisions
"We don't want it to slow down our current processes just to say we're using it," Isaac noted. "We're looking for ways to supplement and enhance our business."
The Bigger Opportunity: Where AI Could Transform Operations
While Isaac is making smart use of AI for specific tasks, there are massive opportunities he—and many small business owners—haven't fully tapped into yet. Let's break down where AI could save him dozens of hours per week across both businesses:
Property Management Goldmine
Tenant Communication at Scale: Instead of his assistant property managers handling every maintenance request email manually, an AI system could categorize urgency, route requests to the right team member, and even draft initial responses for approval. This doesn't replace the human touch—it amplifies it.
Predictive Maintenance Scheduling: With data from dozens of properties, AI could analyze patterns to predict when HVAC systems need servicing or when appliances typically fail, allowing proactive maintenance instead of reactive emergencies.
Lease Analysis and Compliance: Isaac mentioned tracking key metrics like occupancy rates and maintenance costs. AI could automatically flag lease renewals 90 days out, identify properties underperforming on rent-to-market value, and ensure compliance across different HOA requirements without manual tracking.
Coffee Shop Optimization
Isaac already tracks granular metrics—toppings per ice cream scoop, small vs. large drink ratios, inventory patterns. But here's where AI could take Screaming Cat to the next level:
Inventory Forecasting: AI can analyze historical sales data combined with external factors (weather, local events, day of week) to predict exactly how much milk, coffee beans, and ice cream to order. This reduces waste and prevents stockouts during rush periods.
Staffing Optimization: Instead of manually creating schedules, AI could analyze traffic patterns and suggest optimal staffing levels for different times and days, ensuring coverage during rushes without overstaffing during slow periods.
Dynamic Menu Engineering: By tracking which items sell together and at what times, AI could suggest menu adjustments, upsell prompts for staff, or even dynamic pricing strategies for off-peak hours.
The Real Business Owner's Perspective on AI
What stands out most about Isaac's approach is his pragmatism. He's not chasing AI for the sake of innovation. He's not trying to replace his team with robots. He's looking for genuine efficiency gains that let him focus on what matters: growing the business and maintaining quality.
"It's things that supplement and help us," Isaac said. "Everyone is trying to find what's the best use cases."
This is the right mindset for small business owners. AI isn't about wholesale replacement of human judgment—it's about removing the tedious, time-consuming tasks that prevent you from focusing on strategy, customer relationships, and growth.
The System Builder's Advantage
One crucial factor in Isaac's success—and his potential to leverage AI even more—is that he built his businesses with systems from day one. He didn't just open a coffee shop; he built it with processes as if he were planning to open ten locations.
This is critical for AI implementation. AI tools work best when they can plug into existing systems and processes. If you're running your business off memory and scattered spreadsheets, AI can't help you. But if you have documented workflows, clear metrics, and organized data, AI becomes a force multiplier.
"We're taking the approach of setting this up with the potential to scale," Isaac explained. "If you have that mindset of growing this as a large operation with multiple locations, you really have to get all the processes down correctly in the first spot."
Actionable Takeaways for Small Business Owners
Whether you're managing properties, running a coffee shop, or operating any service-based business, here's what you can learn from Isaac's journey:
Start with one high-impact use case. Don't try to AI-ify your entire operation overnight. Pick one repetitive, time-consuming task and solve it first. For Isaac, it was document analysis. What's yours?
Know your numbers first. AI can't improve what you don't measure. Isaac tracks everything from toppings-per-scoop to property maintenance costs. That data becomes the foundation for AI-driven insights.
Build for scale, even if you're small. Document your processes as if you're training a new employee. That documentation becomes the training data for AI tools later.
Keep the human touch where it matters. Isaac's team still manages client relationships personally. AI handles the background work so humans can focus on the high-value interactions that actually differentiate your business.
Stay curious but skeptical. Isaac explores AI tools actively but doesn't implement anything that slows down current operations. Test, measure, and only adopt what genuinely helps.
The Bottom Line
Isaac and his wife have built two successful businesses by working smarter, not just harder. They started by replacing themselves in day-to-day operations through team building and systems. Now, they're in the early stages of using AI to take efficiency to the next level.
The opportunity for small business owners isn't in some distant, sci-fi future. It's available right now, in practical applications that save hours every week and free you up to focus on growth, strategy, and the parts of your business that actually require human creativity and judgment.
You don't need to be a tech expert. You just need to be willing to experiment, stay curious, and approach AI the same way Isaac does—as a tool to supplement and enhance what you're already building.
Want to hear more from entrepreneurs like Isaac who are navigating the intersection of traditional business and emerging technology? Subscribe to The Hey Chat Podcast and follow us for weekly insights into real businesses, real challenges, and real solutions.
