May 31, 2018 · 48m · y-combinator
Advice for Students and Recent Graduates on Finding Jobs – Liz Wessel of WayUp · Y Combinator
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In this Y Combinator podcast interview, WayUp co-founder and CEO Liz Wessel shares her entrepreneurial journey from college projects to scaling a national hiring platform, alongside actionable career advice for students and job seekers.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
The partners as informed peer 2.5 Guest teaching 2.4 Guest disagreement 0.5 The partners pushing back 1.3
speaking balance: gold is the partners, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:46 Dismissing career office advice
Liz bluntly dismisses common college career advice to only apply to a few jobs, telling students that approach is flat wrong.
Hardest push from the partners ▶ 36:04 Craig challenging management styleCraig challenges Liz's framing by suggesting she simply built the entire company around people who match her Type A personality.
Biggest teaching moment ▶ 17:15 The REAF interviewing frameworkLiz systematically educates listeners and the host on her four-step framework for crushing job interviews.
The partners hold their own ▶ 11:00 Casey Neistat email filter exampleCraig demonstrates practical insight by referencing Casey Neistat's Gmail filter rules to explain why vague meeting requests fail.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The partners as informed peer | Guest teaching | Guest disagreement | The partners pushing back | Why |
|---|---|---|---|---|---|---|
| Liz Wessel's First Entrepreneurial Venture: Penn Eats | 2 | 1 | 0 | 1 | Craig prompts Liz to explain how she got into entrepreneurship. Liz narrates founding Penn Eats and how a college project evolved into WayUp. | |
| Leaving Google and Advice from Sequoia's Roelof Botha | 2 | 2 | 0 | 1 | Craig asks how Liz decided to leave Google despite the comfort of corporate tech. Liz explains the APMM program and receiving cold email advice from Roelof Botha. | |
| Cold Emailing Strategies and Best Practices for Students | 4 | 3 | 1 | 1 | Liz shares tactical advice on cold emailing while Craig contributes practical tips from his own experiences and Casey Neistat's email habits. | |
| Liz Wessel's Daily Schedule, Sleep Habits, and Health Routine | 2 | 1 | 0 | 1 | Craig asks about Liz's notorious schedule and minimal sleep routine. Liz clarifies that her low sleep requirement is purely genetic and not a badge of honor. | |
| Common Questions from Student Founders and Job Seekers | 2 | 4 | 1 | 1 | Liz outlines the key questions student founders ask and walks through her REAF framework for interviewing, debunking conventional college career advice. | |
| Developing Communication Skills and Memorable Interview Tactics | 3 | 2 | 1 | 2 | Craig questions whether intense candidate research crosses into being oppressive or creepy. Liz explains how to balance enthusiasm with genuine conversation. | |
| Finding and Partnering with Co-Founder JJ Flegelman | 2 | 2 | 1 | 2 | Liz explains how she found her co-founder JJ by examining hackathon applicant data. Craig asks how she vetted technical ability without an engineering degree. | |
| Scaling WayUp: Management Challenges, Hiring, and Founder Dynamics | 3 | 4 | 1 | 2 | Liz discusses the immense difficulty of management and hiring senior talent. Craig presses on whether Liz built the company strictly around personalities she personally manages well. | |
| WayUp's Unique Value Proposition and Targeted Content Strategy | 3 | 3 | 0 | 1 | Liz details WayUp's three core platform pillars and targeted content strategy. Craig connects her points to his own content challenges at Y Combinator. | |
| Evolving Higher Education Trends and Early Startup Hiring Advice | 2 | 2 | 0 | 1 | Craig and Liz discuss shifting hiring norms where employers prioritize skills and curiosity over specific college degrees. | |
| 10-Year Goals, Treating Career Like Marriage, and Job Satisfaction | 3 | 2 | 0 | 1 | Liz shares advice comparing career selection to choosing a spouse and urges students to test roles early. Craig agrees based on his own early internship experiences. |
Statements from this episode (15)
Wessel: Sold thousands of Penn Eats discount cards for $15 each
“I called it the Penn Eats card, and I sold, I got back to campus in my junior summer, I hired all my friends to basically go around selling these cards for 15 bucks a pop, and we sold, like, thousands”
Wessel: Google APMM program hires 25 to 50 US students annually
“They hire, like, 25 to 50 U.S. College students each year to be in this program, and it's filled with alumni who have started unbelievable businesses.”
Botha via Wessel: Google offers premier operating experience for future founders
“Google is one of the best operating companies in the world, tech companies especially. You'll be surrounded by great managers, great engineers. You'll meet great talent that you might hire one day.”
Wessel: Maximize cold outreach because people stop helping once you graduate
“No one doesn't want to help college students. I feel like the second you graduate, you lose this huge, Badge of pride that you get to say, I'm a college student, and the second you graduate, like, people are much less likely to help you. So use it and abuse it…”
Casey Neistat uses a Gmail filter to trash 'pick your brain' emails
“We did a podcast with Casey Neistat about a month ago and He literally has pick your brain as a Gmail filter to trash.”
Wessel: Executives can answer quick email questions, not 20-minute calls
“Literally my calendar starts at eight AM and stops at one AM almost every day, five to six days a week. And so for me, 20 minutes on calendar is actually a really big deal. Asking me an email that I can just answer on my walk from, you know, one meeting to ano…”
Wessel: Starting a Business Has Become Ubiquitous Among US College Students
“Now I feel like it's a prerequisite to graduating from college in the U.S., or at least at Penn. It just seems like everyone's starting businesses which is funny, because it's not like I graduated so long ago.”
Wessel: Knowing more about a company than the interviewer guarantees impressing them
“If you show up to an interview and you show that you know more about the company than the person interviewing you will impress them. Period. End of story. You will impress them.”
Wessel: Post-interview thank-you notes are rare among students and make candidates stand out
“Just send a thank you note. No one, especially college students, tend to do this these days, and it makes you stick out so much and shows this level of professionalism, which really is pretty easy to accomplish by just sending a thank you note.”
Wessel hacked a Penn hackathon database to scout a technical co-founder
“And what I ended up doing was I found my way, snuck my way into, I think in YC they would call it, they hacked your way into the database of every single person who signed up, where I could see their resume and all of their information. And you were not suppos…”
Wessel: WayUp raised $9 million before hiring its first VP
“At that time, we'd only raised nine million dollars, which is still, I know, it sounds like a lot, but that's not enough to ensure that you are going to be You know, around for years and years to come.”
Wessel: Direct reports to WayUp CEO must be Type A
“If you're working for me there's a few things that you have to have in personality type that I won't I wouldn't hire you to work for me directly. And it's fine to work for someone else, but I'm not gonna hire you to work not for me if you don't, for example, i…”
Wessel: HR tech still struggles with basic applicant tracking system integrations
“HR tech is pretty behind the times. I mean, we're sending men and women to space, and yet we're still, like, really struggling to get applicant tracking system integrations in place.”
Wessel: Untested college expectations drive early-career job switching
“Most commonly when I see people switching their first full-time job within less than a year, which a lot of people do, as you know it's often because they just never had an opportunity to try it out in college, so like, try out everything in college.”