Interview with the Founder: The Vision Behind Calendar.live

Intro: We sat down with the founder of Calendar.live to talk about the product journey, design decisions, and where scheduling meets human behavior.

We built the product to be the part of your day you do not have to think about. It should simply make it easier to do the right thing.

Q: What motivated you to start Calendar.live?

A: The initial spark came from the frustration of living in a world of emails and back and forth to schedule a single meeting. We noticed teams spending hours coordinating time instead of doing the work. The original aim was simple: reduce those minutes to seconds while preserving human convenience.

Q: What was a surprising early challenge?

A: Time zones were far nastier than we imagined. Handling ambiguous user preferences, travel, and working hours required careful UX decisions. Another early surprise was the cultural dimension. People interpret calendar space differently; some guard it religiously, others treat it as public whiteboard. That shaped our permission defaults.

Q: How do you think about privacy and user control?

A: Privacy is baked into design. Users own their data and decide what others see. We default to minimal exposure, with clear toggles for sharing availability. Also, audit logs and enterprise controls provide transparency for organizations that need it.

Q: On AI features, how do you balance automation with user autonomy?

A: Our approach is assistive, not prescriptive. AI suggests and explains why a slot works. The user always retains final approval. The trust model is key: the assistant must earn the right to make proactive changes by demonstrating accuracy and respecting user preferences.

Q: What product decision do you still consider bold?

A: Shipping offline first for calendars was unusual, but it was the right call for professionals who travel. It was technically challenging, but it removed a frequent pain point and improved reliability perception.

Q: What do you want Calendar.live to be in five years?

A: We want it to be the default meeting conductor for knowledge workers. Not just a scheduler, but an organizer that helps teams allocate attention and get better outcomes. That includes better meeting quality, cross system automations, and summarization features that condense meeting noise into meaningful action.

Rapid fire

• Favorite productivity ritual: a 20 minute morning planning session
• Biggest influence: Design thinking applied to collaboration
• Advice to founders: Solve a real daily pain, not a vague inefficiency

Closing thoughts

The founder emphasized that calendars are social objects. Building a product that respects human rhythms, reduces cognitive load, and enhances collaboration requires more than engineering; it requires empathy and iterative listening to users. Calendar.live aims to be that empathetic layer.