Ten years ago, we spent six months planning a two-week trip to Italy. Not because we wanted to – but because we had to.
Hundreds of browser tabs. Research scattered across blogs, forums, Reddit threads and endless screenshots. Bookings confirmed through multiple email addresses and texts. Reservation numbers buried in WhatsApp messages. Everything copied into Google Docs and Excel spreadsheets that we constantly updated, shared and revised... it was an organized disaster.
The day before we left, Shane spent two hours hunting through emails for a single confirmation number.
Sound familiar?
We loved the trip (got engaged in Cinque Terre! 💍), but we couldn't shake one thought: Why doesn't something exist to fix this?
After years of the same frustrating routine – and watching friends struggle through identical chaos – we decided to build it ourselves. Not another booking site. Not another generic itinerary template. But a true travel companion that does the heavy lifting while keeping you in control.
Named after Leif Erikson, the Nordic explorer who discovered America – fitting, since Cali's family is Nordic and we call the US home. Just as Leif charted new territories, we're here to help you explore yours.
Ask Leif brings everything together in one place. AI handles the research, suggestions, and organization. You get a single dashboard with your flights, reservations, confirmations, tickets, notes – everything you need, exactly when you need it. No more email archaeology. No more spreadsheet gymnastics.
Whether you're planning a weekend getaway or a three-week international adventure, our mission is simple:
Less time planning. More time experiencing.