On AI, discomfort, and building human-centric companies

I've never fit into a single box. I'm a guitarist who built a career in law, an attorney who became a software executive, and a product leader who has helped multiple companies grow from nascent startups into nine-figure success stories. On my personal site I joke about being the geek with long hair in high school, but the longer story is simpler: I've spent my career translating vision and design into products that help entrepreneurs succeed.

I scaled Infusionsoft (now Keap) from $1M to $100M in revenue as its CTO and head of product. I drove OfferPad to $100M in revenue as president. As COO of Paradox, an AI recruiting platform, I oversaw 1,000% growth and the support of more than 1,000 global clients. Across those ventures we raised more than $500M in growth capital.

Those results could easily make me an evangelist for technology alone. My leadership philosophy is different. Discomfort is essential to growth. At Infusionsoft I learned to press leaders not about a new hire's résumé but about what made them remarkable — and eventually distilled it to a simple principle: the best leaders push ideas out rather than waiting to have information pulled from them. And in the work itself: version one is always better than version none. Get something viable into the market, learn from it, and iterate. Human judgment, courage, and speed matter as much as the technology.

AI delivers the most value when it clarifies and accelerates human decision-making — not when it tries to replace it.

Human-centric AI

After two decades building cloud and AI companies, I see artificial intelligence as a force multiplier, not a replacement for human leadership. I joined Paradox to build Olivia, the company's AI assistant, because I believed automation could free recruiters to spend more time with candidates. That belief aligns with create human's founding philosophy: AI should assist, automate, and ultimately augment human potential — not eliminate it. My legal background (Arizona State Bar, U.S. Supreme Court) sharpens my sensitivity to ethics and compliance, and it informs my insistence on thoughtful governance.

In practice, AI delivers the most value when it clarifies and accelerates human decision-making. By codifying expectations for a role or a product release, leaders create a version one that AI can support. By encouraging teams to push information upward, leaders ensure that AI augments judgment rather than replacing it. AI can assist by collecting data, automating routine tasks, and surfacing insights — but executives still have to ask the hard questions, define the success metrics, and embrace the discomfort.

Building organizations where humans become greater

Scaling SaaS companies has given me a particular view of the promise and perils of AI. Buying AI tools does not guarantee growth. Integration into core workflows and alignment around a clear operating model are what matter. At Paradox, growth came from focusing on the human experience of recruiters and candidates — not from technology alone. At OfferPad and Infusionsoft, success depended on shipping viable products quickly and learning iteratively, not on chasing perfection.

Three takeaways for leaders

• ·Start with people, not tools. Define what success looks like for each role and process. Use AI to assist by capturing data and automating repetitive tasks, but keep humans at the center of decision-making. Without clear expectations, AI will amplify misalignment rather than solve it.
• ·Embrace discomfort and iteration. Don't wait for perfect data or perfect models. Ship a version one, learn from it, and empower your team to push ideas upward. AI thrives in organizations that learn quickly and aren't afraid to experiment.
• ·Governance matters. Compliance and ethics are not afterthoughts. Whether you're using AI to automate recruiting or to augment customer service, make sure your models and processes respect privacy, fairness, and transparency. Trust is the foundation of every long-term relationship, and AI should strengthen it — not erode it.

The goal is not to build systems that make people smaller. It's to build organizations where people become greater — one version at a time.