Founder spotlight: Nowadays' Anna Sun on turning event planning headaches into AI innovation

During her final year at MIT, Anna Sun found herself on the phone negotiating with ice cream vendors, sorting out how she was going to secure enough frozen treats for her class of over 1,000 students. 

As both a computer science student and class president at MIT, Anna spent much of her college years organizing large-scale events for her fellow students. “I was spending my weekends calling venues and doing back and forth negotiations with the Boston Aquarium,” Anna says. One particularly memorable weekend had her personally picking up 2,000 McDonald’s McNuggets because there wasn’t a simple solution for bulk delivery. 

Executive assistants and people leaders everywhere know this struggle. Corporate event planning—from holiday parties to offsites—involves countless hours of manual coordination. With today's distributed teams, these gatherings have become even more essential for employee engagement and culture building. According to GBT, 60% of meetings this year will be in-person, with continued growth expected.

This challenge led Anna to team up with her older sister, Amy Yan (also a former class president at her respective university, Johns Hopkins) to create Nowadays—an AI co-pilot that automates the heavy lifting of event planning. Their technology reaches out to venues and vendors, manages emails and calls, handles negotiations and maintains budgets, eliminating  time-consuming manual work.

Since launching in May 2024, Nowadays has booked over $7M worth of events for teams like Google, Amazon and Notion across 100+ gatherings worldwide. In December, it raised a $2M party seed round with investors like Y Combinator, Basis Set Ventures, Hike VC and angels. 

Rippling sat down with Anna to talk about her background in event planning, what it was like co-founding a company with her sister, and the aha moment that confirmed the sisters were building in the right direction.

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Who are your customers?

Typically our customers are chiefs of staff, COOs, or anyone who's planning a corporate event. We're focusing on high growth startups from series A to D. 

One of our customers is an open source Firebase alternative, Supabase. We've planned events for them ranging from 100 to 200 people. Right now, they are using our platform to plan their offsite for 100 people in Barcelona. This platform makes a difference—we're able to bring the distributed team together.

Our current customers are mostly corporate events because they have higher willingness to pay and lower churn. But users have actually hacked our systems to plan other types of events. Somebody planned their wedding in Utah and another person planned their father's 50th anniversary. The possibilities are endless, and these use cases prove that we can expand our target audience in the future, as we scale—I can see this being used for bachelorette parties, family gatherings, everything in between.

Can you share a pivotal moment that’s impacted your company’s direction?

When we first had the idea for Nowadays, we envisioned an AI co-pilot for a general personal assistant—not specifically an event planner. We both loved event planning, but we weren't sure if there was a need for an AI-powered tool in that space.

But when we launched, somebody actually paid $500 out of their own pocket for us to plan their 15-person offsite because she had been tasked with the project at the last minute, despite her normal workload. This gave us the confidence to move in a new direction planning events. 

Any advice for founders?

I think the biggest thing that we learned in YC was that the main reason companies die isn't because money runs out or something goes wrong. It's usually because the founders give up when they see how much work this is every day—because it truly is a lot of work. But I think as you stick with it, you'll learn a lot more in this space and you'll just continue growing.

What’s next for Nowadays?

We just brought on a chief of staff, and even more recently, hired our founding product engineer. We believe that founding engineers are a very critical role early on, just because we're a tech company. It's easy to become a services business in the events industry, a trap we’ve seen many competitors fall into. To avoid this pitfall, we want to focus on the tech and automate the entire planning process before scaling.

One of our biggest challenges that we're working on right now is actually learning when to say no to customers, because we realized that with corporate events, there's so many nuances in figuring out what is scalable and what's not. When it comes to deciding which features to pursue and which to leave on the table, here’s what we look for: 

• Have other customers mentioned it before? 

• Does the customer seem excited to pay for it? 

• Can we eventually automate this feature? 

We’re willing to try out any feature manually once as long as it meets all of these criteria. 

Why Rippling?

We chose to go with Rippling because that allows us to focus on building our company and know that payroll and back office work is taken care of. We don't need to spend time on manual work doing payroll and onboarding and those repetitive HR tasks—Rippling handles all that so we can think about strategy and the big picture.