You’ve got one software system that doesn’t play nicely with your other software system—so surely the answer is a third software system to link them together, right? And how about adding a fourth, maybe even a fifth? Paul and Rich discuss the challenging gaps between the platforms people use to manage their businesses: How hard it can be to truly identify problems while you’re trying to grow, and how technology consultants tend to recommend shorter-term solutions that only make things more complicated—and more expensive.

How do you bring in ten times as many new users every day? That’s not the question you should actually be asking. Paul and Rich discuss the tech world’s faulty success metrics, the perpetual struggle of onboarding, and the importance of humility when listening to and communicating with your users.

If a huge company wants to “partner” with your small business, can that ever be a fair partnership? Paul describes a recent mentorship dilemma to Rich, and they discuss the dynamics that make the position of the smaller player in that scenario so challenging. Plus: Musings on public-spectacle trials past and present, Nvidia CEO Jensen Huang, and the existential dread prompted by even the most innocent Slack notifications.