On my first day as a CEO, half my face was swollen from getting my wisdom teeth out — but the 2 meetings I had with investors completely changed my life

Liz Wessel; Business Insider
  • Liz Wessel traded her job at Google for the start-up world.
  • In July 2014, she and her co-founder, JJ Fliegelman, began building a company to help students and young professionals find jobs and internships.
  • On her first day as CEO of WayUp, Wessel arranged two meetings with prospective investors – the only problem was that half of her face was swollen from having her wisdom teeth removed.
  • Wessel explains how, despite that setback, her pitches led to a seed round of almost $US1 million.

My first day as CEO ofWayUp(then called “The Campus Job”) was in July 2014. The day before, I had handed in my rainbow-coloured badge to Google and said goodbye to the free lobster and my insanely smart colleagues.

But I had no hesitations or fears. I knew leaving one amazing job would be worth it to build this business – one that we hoped would help millions of students find jobs and internships.

I also had just gotten my wisdom teeth removed, leaving half of my face resembling that of a chipmunk. This was especially terrible because on this first dayworking on my new company, I had my first two fundraising meetings – one withAnu DuggalofFemale Founders Fund, and the other with David Tisch and Adam Rothenberg ofBoxGroup. I’d been preparing for both meetings for what felt like my whole life, and now I was showing up with a half-swollen face. How lovely.

After waking up, I went straight to my computer to check out the code that JJ Fliegelman, my cofounder, had deployed that morning at 6:00 a.m. He pulled an all-nighter so that we could get a basic website up and running in time for my investor meetings. While we didn’t yet have a full product, we at least had a prototype I could show.

Impressed by all of the new functionalities that 24 hours prior had just been drawings in my notebook, I went off to meet Anu at Soho House. Armed with only my laptop and a notebook, I arrived at the dark hotel lounge looking for Anu – we had never met in person, though I had seen pictures online.

Suddenly, a friendly woman waved at me and smiled. All I could think about was making sure that my hair covered the swollen half of my face so she wouldn’t notice my chipmunk cheek. I sat down and told her about our business, and pitched her on our vision. I navigated through the slides, which included stick figure men and grand visionary statements.

At the end of the hour, she assured me I’d hear from her right away with an introduction to her colleague, whom she wanted me to connect with for a second meeting.

She also offered to introduce me to another top NYC seed investor,Lerer-Hippeau Ventures. I couldn’t decide if this was a good idea or a bad one – on one hand, I’d kill for a meeting with Eric Hippeau. On the other hand, I’d been told not to get introductions to investors from investors who haven’t already invested themselves. And she technically hadn’t committed in that moment, which sometimes in investor code means rejection (or so I had been told). Nevertheless, something about Anu made me trust her – a good choice, in hindsight – and I decided to take her up on her offer.

Next up was BoxGroup. I was more nervous about this meeting than I’d ever been in my life. It was with the founders, David Tisch and Adam Rothenberg, who I’d heard lecture back when I was in college, and whose investments I’d been tracking for years.

I showed up at their office, surprised by how intimate and non-corporate it was – just a big white room with white globes hanging from the ceiling. And then I saw them: David and Adam. My stomach dropped.

I went into a room, walked them through my pitch, and the questions began:

Was the design supposed to look like the site was built in the 1990s?No. That was temporary until we could afford a designer.

Where was JJ and why was I alone?(I stumbled on this for a second – would the truth sound as bad as I thought it was about to?) “…uh, JJ is sleeping. He was up all night coding the site – I can show you it here, actually.”

How much was I raising?“Probably only $US250,000.”

How would we grow?“By hiring Campus Ambassadors from our own platform.”

The questions continued one after another, until I realised that they were interested – like, really interested. They said they liked the idea and had long believed someone should disrupt this space by connecting employers and students directly, without needing to rely on the university alone. They said they’d even be interested in turning the round into a bigger one – but they needed to meet JJ. They asked if I could I bring him back a few days later to meet them as well. We scheduled the meeting, and that was that.

Looking back, that first day was more life-changing than I could have guessed. Not only did David and Adam end up leading ourseed roundfor almost $US1 million (of what has grown to almost $US30 million dollars fundraised), but Anu and Lerer-Hippeau also were huge parts of the round, and have continued to be important and supportive investors since then.

After those meetings, I went back to JJ’s apartment, where we were working that day. He’d woken up and was furiously typing code, building the next feature on our roadmap. I told him about the meetings, we celebrated with a high-five, and we got right back to work. After all, there were millions of students out there who were freaking out about their student debt and career aspirations, and there was nothing more we wanted than to help them.

Liz Wessel is obsessed with helping people get hired. She is the Co-Founder and CEO of WayUp, the go-to platform for millions of early-career professionals to explore opportunities, receive advice, and get discovered by employers. Founded in July 2014, WayUp is a venture-backed startup based in NYC and was named by CNN as one of the 30 most innovative companies changing the world. WayUp has worked withtop companies-including Fortune 500s, startups, and nonprofits- to help them reach, recruit, and engage with the next generation of talent.

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