The Small Business Black Holes with Alan Pentz
Flying Backwards: The Case for Real-Time Business Intelligence
July 15, 2025
What if we told you that Michael Dell—yes, the tech billionaire—still worries about cash flow? In this eye-opening episode, Elizabeth Gore, co-founder of Hello Alice, shatters conventional wisdom while revealing why 1.5 million entrepreneurs trust her platform. Gore exposes uncomfortable truths: growth can actually kill your business, traditional credit scores are broken, and every business needs six months of operating expenses banked—not the typical three most advisors recommend. From veterans with "terrible credit but perfect business planning" to Main Street entrepreneurs drowning in unusable data, Gore's radical solution involves AI-driven intelligence, open banking, and $60M in grant distribution that's reshaping how we fund small businesses. This isn't just another funding conversation—it's a masterclass in recognizing that your biggest opportunities often masquerade as your greatest threats.
In this episode of Small Business Black Holes, Elizabeth Gore, co-founder of Hello Alice, reveals why even Michael Dell loses sleep over cash flow and how her platform serves 1.5 million entrepreneurs navigating America's most counterintuitive business challenges. Gore argues that growth often triggers fatal cash crunches, traditional credit scores fail real entrepreneurs, and smart businesses need six months of operating expenses banked—double what most advisors recommend.

From AI-driven business intelligence to $60 million in vetted grants, Gore's platform is reshaping how we evaluate and fund small businesses. This conversation exposes why your biggest opportunities often masquerade as your greatest threats and provides actionable strategies for building financial resilience while scaling sustainably.


Key Insights: 


Highlights:


[09:23] Cash Flow Management Strategy - Building a Six-Month Buffer
Elizabeth Gore emphasizes the critical importance of maintaining 3-6 months of operating expenses in the bank, regardless of business size or stage. Cash crunches can occur during both emergencies and growth opportunities, like landing a major retail contract or scaling operations. Smart business owners should pair their cash reserves with a preemptively secured line of credit, even if they don't plan to use it immediately. Small businesses need to practice calculated, measured growth rather than expanding too quickly without adequate financial cushioning. This approach helps weather unexpected challenges while also enabling companies to seize growth opportunities when they arise.

[13:30] Focus on Core Strengths While Delegating Weaknesses
Once businesses reach $1 million in revenue, owners often remain trapped doing low-value tasks that drain their energy and attention. The key to breaking through revenue plateaus is identifying what unique value only you can bring to the business - whether that's sales, product development, or client relationships. Smart owners should invest in hiring experts to handle areas outside their expertise, particularly finance and operations. This allows the business owner to focus on high-impact activities that drive growth. The strategy helps prevent the common pattern of jumping between various operational fires while neglecting strategic priorities.

[16:07] Leveraging AI for Financial Intelligence
Elizabeth Gore highlights how AI-driven financial tools are transforming small business management through real-time P&L insights and cash flow projections. Daily financial data analysis, which was previously impossible for time-strapped owners, is becoming automated and actionable. This technology shift helps owners make faster, more informed decisions about inventory, pricing, and resource allocation. The integration of open banking and AI tools is removing traditional barriers around credit access by focusing on actual business performance rather than just credit scores. These innovations are particularly valuable for underserved business communities who may have strong operations but limited credit history.

[18:49] Strategic Partnership Model for Growth
Hello Alice demonstrates how strategic partnerships can create mutual value between large enterprises and small businesses. By partnering with major companies like Dell and Salesforce, they provide free resources to small businesses while helping enterprise partners reduce customer acquisition costs. This model enables small businesses to access sophisticated tools and support they couldn't afford independently. The approach combines commercial partnerships with philanthropic initiatives, creating a sustainable way to serve underrepresented business communities. Their success shows how building the right ecosystem of partners can help scale impact while maintaining profitability.


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