Jeff MacPherson
CEO
Most founders are asking the wrong question about artificial intelligence.
They are asking, “Which tool should we buy?” Jeff MacPherson believes the better question is, “What already works inside this business, and how can AI multiply it?”
Jeff is a three-time technology founder and the CEO of Cloud37, a company helping experts and professional service businesses transform their knowledge into intelligent systems, scalable client experiences, and recurring revenue without automatically adding more people. His philosophy is refreshingly grounded: AI is not a shortcut around unclear thinking, broken processes, or weak leadership. It amplifies the foundation already there.
That perspective was earned in the trenches. Jeff built what Cloud37 describes as the first Instagram direct-message chatbot, helped create a $2.5 million NFT launch without paid advertising, battled platform disruption, built international teams, and spent years studying why some companies turn technology into leverage while others lose time, money, and trust chasing the latest shiny object.
Behind the AI conversation is a deeper founder story about resilience, vulnerability, reinvention, and what happens when the technology changes faster than the identity of the person leading the company.
Jeff is not simply asking what AI can do.
He is asking what remains uniquely human once AI can do almost everything else.
