Awareness Technologies

Brad Miller had proven himself as a capital-efficient operator, previously scaling SilverSky from startup to $60 million in revenue and $10 million EBITDA before a Goldman Sachs acquisition valued at $150 million (later sold to BAE for $250 million). When his then-employer stopped wanting to acquire additional companies due to consolidation concerns, Miller asked permission to pursue deals they passed on. When denied, he left to pursue Awareness Technologies independently with a financial partner.

Miller and his co-investor each contributed $2.75 million (50-50 equity split) to acquire Awareness Technologies in 2010. The business was generating $5 million in revenue but losing $1 million annually. Critically, though structured as a SaaS cloud delivery model, the founders were only charging one-time fees despite providing service and cloud infrastructure indefinitely. Miller's first move was simple but transformative: convert to a subscription model. "The business went from $5 million, losing a million to $7 million, making a million because the extra $2 million of immediate revenue was pure profit." This immediate profitability shift, achieved without building new product, demonstrated the power of business model optimization.

Awareness Technologies operated in the employee monitoring and PC activity tracking space, serving both B2B and consumer markets. The company acquired complementary businesses along the way—buying a consumer business and a B2B business for $1 million each, then $3 million and $3.5 million respectively. The most transformative acquisition came when Miller identified a competitor doing $15 million in revenue with 40% EBITDA margins. Two VCs had previously bought this competitor for $45 million, but mismanagement caused revenue to collapse to $7 million while losses mounted to $3 million annually. Miller had wanted to acquire this business a year earlier when it was thriving but couldn't afford it at that time. When the VCs' investment deteriorated and they faced payroll challenges, Miller was positioned to strike. "They viewed us as the small guy nipping at their heels and not able to afford them," but as they burned cash and couldn't secure better alternatives, opportunity emerged. Miller closed the acquisition in three weeks by assuming a $2 million line of credit the VCs had guaranteed, with no cash changing hands.

Miller's strategy centered on finding "things that are doing well in spite of some mistakes." He recognized that founder-operators often excel in certain domains but miss obvious improvements in others. The subscription model fix was one example—founders had built cloud infrastructure but hadn't monetized it recurring. For acquisitions, Miller looked for strong competitive positions, healthy margins, and fixable operational problems. The COVID-19 pandemic proved fortuitous; Awareness Technologies' B2B employee monitoring business surged as companies navigated remote work, with the business answering the critical question: "How do I get comfortable with all the things that I used to see with my eyes when people came to the office?"

Financing proved challenging in traditional VC circles. SVB wouldn't touch the business because it lacked a "famous" VC investor, dismissing profitable cash flow generation as irrelevant to their mandate. Instead, Miller partnered with Webster Bank, a local Connecticut community bank with whom he had built a personal relationship through his prior company. This relationship-based banking provided 3-3.5x leverage on EBITDA at approximately 5% interest (LIBOR plus minimal spread), enabling acquisitions funded entirely through bank debt against cash flow generation.

By the time of sale, Awareness Technologies had grown from the initial $5 million revenue to $20 million in annual revenue, with approximately $6 million in EBITDA. Miller and his co-investor had extracted $12.5 million in dividends along the way while maintaining a profitable, debt-efficient business. The combined proceeds from dividends and the exit sale totaled just shy of $50 million, delivering approximately 9x ROI on the original $5.5 million investment. Miller remained committed to the leverage-and-optimize playbook, acknowledging that "every deal has its own... It's not always the same playbook for each deal, right? It depends on the market dynamics, the growth trajectory, the competitive."

The exit demonstrated extreme capital efficiency: initial cash exposure of approximately $2.7 million ($5.5 million acquired, $2.75 million borrowed by each partner) yielded returns approaching $50 million through operational excellence, strategic acquisitions, and favorable market timing during the remote-work transition.