What It's Like To Prepare For 'Demo Week' At Y Combinator

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Y Combinator is one of the most competitive startup incubators in the country. 

Thousands apply, but only 47 startups are in the current class.One of those startups is StyleUp, co-founded by Kendall Herbst and Ryan Choi. The site is essentially a style assistant: Every morning, users get an email with an outfit that matches their personal style and works with the local weather. 

“We help women who are interested in fashion but don’t have time to read a 500-page magazine,” says Herbst, who met Choi at MIT Sloan and moved from Cambridge, MA to Mountain View, CA this January to attend Y Combinator.

The intense three-month program culminates in “Demo Day,” where startups pitch to investors, which was on Tuesday. Herbst took a camera around with her this past week and offered to share her experience with Business Insider.  

You can follow Kendall at @kendall_to_go.

8 AM: After waking up, I immediately check out StyleUp's progress: how many new members we've added, how many women liked their styles from the day before, etc. I co-founded the site with Ryan Choi, an early engineer at Salesforce, whom I met at MIT Sloan.

I read all the user comments on our website. They serve as a daily report card of how well we're doing.

9:15 AM: Normally, I'd just continue working on StyleUp, but Fridays are lighter, so I take the time to jog instead. They tell you at the start of Y Combinator to fit some healthy habits into your life; three months is too long to exist on crummy food, no sleep and no exercise.

10:30 AM: I head over to the Y Combinator office to meet Ryan. The plan is to practice our Demo Day pitch over … and over … and over. This 2-minute talk is your first impression to hundreds of investors, so you should know what you're doing.

12 PM: I love getting feedback from other co-founders on our presentation. Since they're more removed from your business, they're honest about what parts are unclear or what parts you should emphasise more. Here I'm talking with the great guys at Meldium, a password manager for teams.

1 PM: I'm back to practicing, incorporating some of the notes from fellow founders and Y Combinator partners. I'm told it's normal to have some changes, so it doesn't freak me out. Or maybe after the long hours we've put in for the past three months, I'm just too tired to get that freaked out.

Y Combinator overall is pretty laissez-faire. You meet up collectively as a batch only once a week for dinner. Now that we're nearing the end, we see each other a bit more often. It's interesting to talk about the progress you're each making or similar obstacles you're facing. You can learn a lot from people far outside your particular industry. Here I'm catching up with Mike Robbins, co-founder of CircuitLab, which makes web-based electronics design software.

5:45 PM: I grab some takeaway sushi as I head home. It's fast and it's healthy.

A stroll down Dana St. in Mountain View is beautiful with lemon trees and flowers everywhere.

7 PM: My co-founder and I start a Google Hangout with our designer Nathalie who lives in Montreal. She was a StyleUp user who liked our service so much that she reached out to see if she could get involved. We like her aesthetic, so she has become our new go-to person for cool design projects. Here we're talking about StyleUp's mission overall and our pitch for Demo Day.

8 PM: I update our blog with an interview with a J.Crew executive: StyleUppers love J.Crew so hopefully our members will enjoy the inside access. I also review Special Event requests, which are for when women have big events they want to shop for. Our users tell me how they want to look and what their budget is and I track down three great options.

10 PM: I catch up on some emails, but I'm exhausted. Being so focused on StyleUp and working out of my apartment solo can make you feel a little crazy. You need some kind of outlet when concentrating like this, so I'll put on some pop music or listen to standup comedy on YouTube while I work. Sometimes I'll just take photos of myself going crazy and text them to my friends. They seem to understand.

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