Turning Events Into Reservations · Sarah Klingman, Mostest

What we talked about.

In this episode, Sunny Ray talks with Sarah Klingman, founder of Mostest, about turning event planning into a seamless booking experience. Klingman explains that while restaurants, hotels, and flights can be booked in seconds, corporate events still rely on forms, emails, and phone calls, a gap she experienced firsthand while planning her own wedding and later organizing events at work. She shares how her retail background at Adidas, including running the Foot Locker account and leading a business worth over 200 million dollars, shaped her approach to negotiation, partnerships, and understanding what customers actually want versus what draws them in. Klingman discusses building Mostest's first product with Zapier and Squarespace, shifting from an hourly pricing model to outcome based pricing, and training AI on thousands of planner memos to combine automation with human taste and judgment. She also touches on raising early funding from Wildwood Ventures and Q Capital, avoiding vendor kickbacks, and targeting the long tail of corporate events under fifty thousand dollars as Mostest works to capture a share of a market projected to reach 1.6 trillion dollars over the next decade.

Mostest founder Sarah Klingman on turning event planning into instant reservations, blending AI and human concierge service.

The questions, and the answers.

What is Mostest and what problem are you solving?

You can book a table or a hotel room in seconds, but planning an event still means forms, emails, and phone calls. We believe planning an event should be as easy as booking a reservation. Mostest lets people go from idea to booked event, whether fully through AI or with a dedicated concierge planner, without the usual friction.

You ran the Foot Locker account at Adidas. What did that teach you?

I learned the art of negotiation and how to drive B2B partnerships inside a consumer facing brand, which has been key at Mostest since we sell to enterprises while staying consumer friendly. It was high pressure and high visibility, with a lot of bureaucracy to navigate, which honestly wasn't so different from being a founder.

When did you first think event booking couldn't possibly still work this way?

It was my own wedding about a decade ago. It was the most expensive thing my family had ever purchased, and there was nothing tech enabled to help, just marketplaces that left all the research to me. After planning events for the ninth and tenth time, mostly at work, I decided someone had to fix this, and it might as well be me.

Why did you start with a transaction rather than AI?

When we started three years ago, AI wasn't commercialized yet, so I focused on democratizing access and supercharging planners with technology first. Starting with a real transaction turns Mostest from a theoretical bet into a growth plan built on monetizing demand we've already proven exists, rather than betting everything on an unproven AI thesis from day one.

Your first pricing model was hourly. What broke, and what replaced it?

Hourly just doesn't work because companies are deliverable focused, not hour focused. Tracking hours required a huge investment in logistics management, and it misaligned incentives, since planners wanted to rack up hours while companies just wanted results. We moved to aligning around outcomes so everyone working with us shares the same goal.

How do you get a human planner to hand work to a model?

We trained our models on thousands of memos written by real event planners, covering how they evaluate venues and vendors, manage budgets, and send timeline nudges, so it acts like a planner in your pocket. Creativity and boots on the ground for bigger or more complex events still need an accountable human, and we don't see that going away.

You raised early from two firms instead of one big round. What did that teach you?

My first check came from Wildwood Ventures after someone tagged me in a LinkedIn comment about backing female founders. I was an LLC with no real product, but they saw the traction and got excited about helping me find the right CTO and mentorship. From there Q Capital set terms for our seed round, and Nexus Global and TS Squared joined as investors.

Zero vendor kickbacks is a stated principle. What did holding that line cost you?

It has cost me plenty of tough investor questions. We want it frictionless for venues and vendors to join the platform, and we're still learning how to create value for them day to day, so we don't feel we've earned the right to charge them yet. Giving them instant bookings through direct calendar integration is the edge we can offer today.