Building a Profitable Business in the Age of AI with Don Gregori

Technology can help a business grow faster, but without the right strategy, it can also become an expensive mistake.

On this episode of Pivot to Profit, Pam Jordan sits down with Don Gregori, Chief Operating Officer of First Factory, a custom nearshore software solutions provider. Don brings more than 25 years of experience in product development, digital transformation, leadership, and AI adoption.

Don’s career began far from the technology world. After studying theater and spending time in the film industry, he joined Kaplan, where an entry-level marketing role evolved into an 18-year career spanning marketing, operations, P&L management, and custom software development. That experience eventually led him to First Factory—first as a client and later as a leader within the company.

Throughout the conversation, Pam and Don explore one of the biggest financial mistakes businesses can make with technology: focusing only on the upfront price. Software requires ongoing maintenance, security, updates, integrations, and improvements as a company grows. Don recommends budgeting approximately 20–25% of the original project cost annually for maintenance, emphasizing that consistent updates can help prevent much more expensive rework later.

That long-term thinking is especially important as businesses adopt AI. Moving too quickly or choosing the cheapest development option can create costly problems when the original strategy, requirements, or guardrails aren’t right. Business owners need to consider scalability, security, maintenance, and return on investment—not simply how quickly or cheaply something can be built.

The conversation also goes beyond software. Don explains why startups should prioritize generating customer revenue instead of pouring every available dollar into product development. A great product alone doesn’t create a successful business. Companies also need sales, marketing, customer service, and, ultimately, profit.
Pam and Don also discuss ideas from his award-winning book, The Emergent Leader, including the importance of running lean, maintaining the flexibility to invest during difficult economic periods, and building a company capable of adapting quickly.

For entrepreneurs navigating AI, software investments, or rapid growth, this episode is an important reminder: technology should support a profitable, sustainable business—not become the business strategy itself.