Third Time Lucky with Kyle Hency

In this episode of 1 to 100, Kyle Hency joins Jack, Jeremiah, and Rishabh to talk about going from $0 to $100M for a third time.

We talk about building high-agency teams, company structure, AI adoption, and how the nature of work is changing.

Kyle describes Chubbies’ early advantage: four highly invested co-founders producing the output of a much larger team. As the company grew to about 125 employees, leadership, structure, and team design became more important.

He compares that experience with GoodDay, which operated in a decentralized way for almost three years. With 24 people, nearly 100 customers, and several functions working at once, the company started centralizing decisions. The challenge is adding process without reducing creativity.

The group talks about how AI changes management. Tools can provide a faster view of performance, coordination, and even the complexity or usefulness of software features. Managers still need human conversations, but they spend less time sorting through competing versions of events.

They discuss the difference between people who need a task list and people who see a problem, take ownership, and finish it. Kyle argues that companies should hire for deep expertise and high agency. Rishabh argues that the number of people who can independently own major initiatives may matter more than company size.

The conversation also covers earned equity, outcome-based incentives, and employees who run side projects. The group agrees that side work is not automatically a problem. The real question is whether the employee brings their best work to the company and whether the company has created work worth committing to.

They close by discussing software interfaces. Rishabh expects more work to move through agents, CLIs, and MCPs. Jack and Jeremiah argue that visual interfaces will still matter, especially for creative work, while Kyle questions how quickly people can absorb constant UI changes.

The lesson for founders is hire people who can own outcomes, use AI to expose reality faster, and add structure without blocking initiative.

Chapters 00:00 The benefits of being CEO 03:59 Scaling Chubbies and building the team 05:06 Centralizing decisions at GoodDay 06:14 Company size and high-agency people 11:29 Founder roles and company structure 13:10 AI and team performance 25:59 Earned equity and incentives 28:23 Side projects and employee commitment 36:19 Software interfaces and agent workflows