Advice for Students and Recent Graduates on Finding Jobs – Liz Wessel of WayUp

by Y Combinator5/31/2018

Liz Wessel is the cofounder and CEO of WayUp. WayUp is a job and internship platform for college students and recent graduates. They were part of the Winter 2015 YC batch.


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Craig Cannon [00:00] – Hey, how’s it going? This is Craig Cannon, and you’re listening Y Combinator’s podcast. Today’s episode is with Liz Wessel. Liz is the co-founder and CEO of WayUp, and WayUp is a job and internship platform for college students and recent graduates. They were part of the Winter 2015 YC batch. All right, here we go. At what point did you know you wanted to start a company?

Liz Wessel [00:24] – My sophomore year of college, I was at Penn and actually started my first business at the end of sophomore year. I went to Stanford for a three-day boot camp called Bases Entrepreneurial Bootcamp, or something like that, and I remember going to the Jamba Juice at Stanford and they asked me, can I see your Stanford ID? And I said, I don’t have one, why? They said, “Oh you’d get like 10 or 15% off your Jamba Juice.” I paid full, because I was a Penn student, but I remember thinking, “Wow, that’s really cool, that’s a great perk for students, I should do this at Penn.” I get back to campus and I walk around to all the restaurants, and I say, “Do you have any loyalty program for students?” They all said no. And I said, “Okay, if I got your logo in the wallet of thousands of students at Penn, would you give them 10, 15% off?” Every single restaurant and bar said yes. And so I said, “Okay and I’m not going to pay you for that or anything and I’m actually going to charge students,” and they were like, “Okay, we don’t care.” I ended up over sophomore summer,

Liz Wessel [01:32] – I also was doing an internship at Blackstone in Tokyo, but meanwhile–

Craig Cannon [01:37] – Okay.

Liz Wessel [01:38] – I was starting, as we all do– But meanwhile, I actually went about hiring this company in China to create thousands of cards that would put the logos of all these businesses on the back. I called it the PennEats card, and I sold, I got back to campus, and my junior summer, I hired all my friends to basically go around selling these cards for 15 bucks a pop, and sold thousands, and it was awesome, and it was very very cool.

Craig Cannon [02:03] – And that kind of gave you the bug?

Liz Wessel [02:05] – I was addicted. I thought the concept of creating something from nothing and solving a problem or helping people, is just such a cool opportunity, and why wouldn’t you want to do that over and over.

Craig Cannon [02:17] – Because you weren’t an engineer, right?

Liz Wessel [02:19] – No, I took a bunch of computer science classes, but I was not what I would call an engineer.

Craig Cannon [02:24] – Were you inherently drawn to creating a software startup or did you try out other ideas?

Liz Wessel [02:30] – That first business, it was like a Wix website and a bunch of plastic cards, so not really much software there. Though I did, to be fair, sell a bunch of cards online. But not much software there. I remember though, my senior year, when I wanted to start that next project, and that’s the one I worked on with my co-founder, now of WayUp, JJ, we very much were keen on having it being a software biz, or an internet company.

Craig Cannon [02:55] – Okay, but you didn’t start it immediately after school?

Liz Wessel [02:57] – Thhe story of WayUp, the high level is my senior year, I’m having to tell the funny version of it from college. The high level is, my senior year, JJ and I worked on a project together that would help college students find campus ambassador jobs and so we worked on that, we launched it, and then I went to Google in California and then I moved to India to lead brand initiatives for Google. JJ went traveling around the world as a backpacking freelancing web developer. As all good backpackers do, went to McKinsey in New York, and so we kept in touch over the years, but that website kept growing and growing to tens of thousands of users and big businesses and so on, and we knew we each wanted to start a company and so we quit our jobs two years after college and started WayUp with the insight that that website we had started in college, which was really just a project, had grown so much. You know at YC, they say make something people want.

Liz Wessel [03:54] – If you build a website that you barely do any marketing work for, and it’s growing that much, then we knew that they had something, and so we shut down that website because it was just a kind of half-assed project, but we took the insights from that and built WayUp off of that.

Craig Cannon [04:09] – Okay, so I’m really curious about how and when you decided to leave Google because a lot of people who could start companies and are in the position, financially they have enough flexibility to leave just kind of get in the cycle. They get a raise every six months or whatever and they stay there forever.

Liz Wessel [04:27] – Yeah, oh man, Google’s a cushy job. It’s an awesome job.

Craig Cannon [04:30] – I’m sure it’s great.

Liz Wessel [04:32] – Super hard but really awesome. I always wanted to start a company full time after college, but my senior year, I applied for, so I’d already done a summer internship between junior and senior year at Google as a product marketing manager intern, I got the offer. I also got the offer at a top-tier VC, venture capital fund, and for me, I’d gotten enough advice that, and I’d started that PennEats company, saw that there was so much I had to learn, whether it was managing people, legal documents, like marketing sales, and for me I basically said, I want one experience that will help me before I start before I start whatever company I one day start. I did not know it was going to be called WayUp. Or that it would be WayUp. I said, I really want to do it for two years. Whatever this job is, I’m going to learn as much as possible for two years, and then I’m going to quit and I’m going to start a company, and hopefully do it with a founder, a co-founder that I love, which I have done. I got these two offers and I didn’t know which one to take, which one would set me up for more success. To start, I said to HR in both of them, I want you to know I’m going to leave this job in two years and start a company, is that okay?

Liz Wessel [05:44] – Google’s so cool. Especially the program I was applying for and that I got the offer to is called the APMM Program, Associate Product Marketing Manager job. The whole program is filled with alumni. 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, Kevin Systrom started Instagram, Brit Morin started Brit and Co., and the list goes on. Some former Googlers, too. Robby Stein was, sorry, some former Googlers. They’re all former Googlers, I was going to say. You know that. I was going to say actually someone from my high school too, but anyway. Robby Stein started a really cool company called Stamp, sold that to Yahoo. Long story short, all these people were in this program. They actually said, it’s totally fine if you leave after two years and start a company. Meanwhile, the VC fund was actually like, yeah we highly recommend that you do VC for two years and then get your MBA or start a company, and this VC fund had many successful founders as well,

Liz Wessel [06:43] – one who just recently had his company go public. I couldn’t choose and so I did what I always tell college students they should do, which is cold email someone who they want the advice from. Roelof Botha was someone who I’d seen speak at the Stanford Bases Entrepreneurial Bootcamp. It’s all going kind of full circle. At the end of the day, I email Roelof Botha and I say, “You are one of the best venture capitalists in the world,” he’s at Sequoia, and I said, “You’ve seen so many successful founders grow huge businesses, I want to be one of those founders, I want the best possible experience I can get beforehand which one would you suggest I do? Go to XYZ fund or go to Google in this program,” and he said I would get the best possible operating experience I could get, and Google’s 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, so go Google, and I did.

Craig Cannon [07:42] – All right, I’ve heard you talk about this in a couple other podcasts.

Liz Wessel [07:44] – I love cold emailing.

Craig Cannon [07:46] – Yeah, me too actually. One of the people I really admired in San Francisco when I was still living in New York, I emailed him, cold emailed him, Skyped him, and I was like, “It’s just so weird, I’m going to be in San Francisco like next week, are you going to be around?” He’s like, “Yeah, I’ll be around.” Then I just bought a flight.

Liz Wessel [08:01] – The best. If you can afford to do that, that’s the best. Entrepreneurs do that a lot apparently, to get venture capital meetings, I thought that was funny.

Craig Cannon [08:07] – It totally works. Say you don’t have a brand name or whatever, you’re just a college student.

Liz Wessel [08:15] – That was me.

Craig Cannon [08:15] – Just like you, exactly. Can you walk us through the steps that you use?

Liz Wessel [08:19] – To cold email? Totally. To start, I have Rapportive on my computer, which is this software that LinkedIn bought. But basically, if you install it into Chrome, and your Gmail, what you can do is you can figure out someone’s email if you can’t find it already online by basically guessing. For example, I don’t remember what Roelof’s email is, but I probably would have looked up Sequoia’s domain, so let’s just say it’s, my guess is it’s probably Sequoia Venture Partners– But let’s just say it’s So I’d look up the domain of the website, and then I’d guess like,, and I’d keep guessing until his image shows up on the right in Rapportive, and that’s when you know you’ve got the right person. Sometimes if they’re a big enough name, you can find their email address online, but if they’re not, that’s the best way to do it. Once you have that, I would say subject line has to be something that’s going to catch their attention,

Liz Wessel [09:14] – so “want to pick your brain” from a college student, not going to stand out. Any college student can do that. My best email, cold email I ever sent was to probably, arguably the most famous woman in business in the country, maybe woman in tech business in the country, I’m not going to say her name and you can guess. My subject line, I saw that she had taught aerobics or done aerobics in high school or college or something, and I had taught water aerobics the summer between high school and college because they pay a lot of money.

Craig Cannon [09:46] – Oh, all right.

Liz Wessel [09:47] – And so, who knew?

Craig Cannon [09:47] – Yeah, I did not.

Liz Wessel [09:48] – I actually like wrote in my email, and I think part of the subject line like “fellow former water aerobics professional” or something silly, but it caught your attention because if you see something ridiculous that someone clearly had to do a lot of research to find out about, they’re going to open the email. Then in the email, I wrote dear blank, and I start off with, “I’m a college student at blank, so in my case, I’m a Penn senior, currently trying to figure out what I want to do with my life between two job offers.” So it just gets to the point of being short, sweet, and here’s who I am. 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, people are much less likely to help you. Use it and abuse it while you’re in college. I get cold emails all the time. I hope I don’t get a barrage of them after this, but I do get a lot, and they always start with I’m a college student at X school.

Liz Wessel [10:47] – Then get to the point, what do you want help with? And ideally show that you’ve done your research, so why are you asking me? In a specific case, for Roelof, I remember I said something to the tune of, you’ve seen so many successful founders. If I had just asked him where should I move, New York or San Francisco, like why would I ask Roelof Botha that, right? I do think that a very big part of your email should be saying why are you asking this person, what do you want from them, who are you, and then show somewhere in there that you’ve done your research and that you’re not just trying to email famous people. If you do those things, you’ll probably get a good response rate.

Craig Cannon [11:22] – We did a podcast with Casey Neistat about a month ago. And he literally has “pick your brain” as a Gmail filter to trash, so I would not recommend picking someone’s brain, I would not recommend asking them out for coffee, or 20 minutes for a phone call. People answer short questions.

Liz Wessel [11:38] – Exactly, and sometimes I get people asking me if I’ll hop on a phone call, and I know it sounds so crazy, but literally my calendar starts at 8:00 am And stops at 1:00 am almost every day, five to six days a week, and so for me, 20 minutes on a calendar is actually a really big deal, ask me in an email that I can just answer on my walk from one meeting to another is not.

Craig Cannon [11:59] – To diverge a little bit, you talked about your calendar, I read online that you don’t sleep a lot, is that true still? How much do you sleep?

Liz Wessel [12:09] – Why don’t I start by just saying this is a genetic thing, most people on my dad’s side of the family don’t sleep a lot, and so it’s not like I’m wearing this with pride and trying to show off. I just don’t need sleep. If I have any sip of alcohol, I do sleep. If I have a glass of wine, I will fall fast asleep, or beer or anything, but assuming I don’t drink, which is most nights, I can go three or four hours of sleep and I’m good to go, and I’ll be just as energetic as right now, I think right now I’m going off of like three, three and a half hours of sleep. Same with my co-founder, but he shouldn’t be like that because he doesn’t have that gene, he’s just crazy.

Craig Cannon [12:46] – Your whole life you’ve been like this?

Liz Wessel [12:48] – In high school, I remember my friend Laura came to me one day and was like, I have a Hanukkah gift for you, and I said what, and she was like, “I’m going to be your assistant because I feel like you never sleep and you have such a crazy agenda and calendar and I just want to help you,” and I was just like, I don’t need an assistant, but thank you. I think I’ve always had like a crazy calendar.

Craig Cannon [13:06] – That’s wild. Given that crazy schedule, do you have any particular health regimens you need to stay normal?

Liz Wessel [13:15] – People are going to judge me, but I don’t work out, I think I’ve been to the gym once in the last year. Twice in the last three years maybe. Maybe a little more than that, I don’t really work out. I love walking around New York, so I guess that’s exercise. I don’t like taking the subway, I love walking. Uber if I’m on a call and I need quiet. But I eat pretty healthy, I don’t like sweets much.

Craig Cannon [13:40] – You’re not on coffee all the time?

Liz Wessel [13:43] – I’m not one of those people who do yoga every day, and by the way, I don’t judge people to do yoga, a lot of my friends do yoga, I’m just not, I don’t know. I hope I live a long life. My family, most people live a long life and most people are about as regimented about their health as I am.

Craig Cannon [13:58] – Walking is very good for you.

Liz Wessel [13:59] – Yeah, there you go. I drink a lot of water.

Craig Cannon [14:03] – Oh, there you go.

Liz Wessel [14:04] – If you sit down with me at a meal, you will hate me because I will ask for two pitchers of water because I will drink water the entire time when I’m not talking.

Craig Cannon [14:09] – We should have more, sorry. More of the tip stuff. What are the most common questions you get when you are getting these cold emails from college students? What tips do they ask for, for internships?

Liz Wessel [14:22] – Probably the most common one, which is an awesome problem to have, is which internship should I choose, which job should I choose, I get that a lot. I wonder if it’s because– The Roelof story, I get a lot of people asking for advice when they’re a student entrepreneur and they’re starting a company and I think that’s amazing. When I started my business in college, I would say I was one of five people I knew who had started companies. 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, I graduated in 2012, but it definitely was not as common back then. That’s another one I get a lot.

Craig Cannon [15:05] – Okay, and so what kind of answers do you give? Is it very specific, or do you have like a mental model for choosing this kind of thing?

Liz Wessel [15:13] – It’s very specific, and often I respond saying, you need to give me more context here. I appreciate if you want to keep the email short, but if you’re, someone yesterday emailed me, I think this student had seen my TED Talk about like eight things you have to do before you graduate, or whatever, and so he emailed me and he said, “I loved your TED Talk, I’m choosing between these two job opportunities, which one should I take?” And I was just like, “I don’t know anything about you, I don’t know what your goals are, I don’t know anything about these jobs, I don’t really have time to look up each job, can you give me more context?” So then he did. It’s nice he tried to keep it short and sweet, but I could only do so much. And what do I know, too? It’s just one opinion.

Craig Cannon [15:54] – Yeah, what about on the actual application site, because I saw you guys have tons of content on your site for students. What are your tips on just preparing yourself to apply for an internship? Assuming it’s very competitive but you have probably the right qualifications for it.

Liz Wessel [16:14] – We really do, it’s, or, we have a ton of content, like thousands of articles. What I will say is, number one, and this is not mean to be self-serving, but we have these profiles on WayUp that are, in my opinion, a much more holistic perspective on who you are versus a LinkedIn profile that’s just your work experience or a resume that people read the bolded words and then ignore the rest. Our profiles on WayUp focus on your Github if you’re an engineer, or your YouTube if you are a performer or a public speaker. Your Instagram if you’re a designer. They show you’re a volunteer, your hobbies, your fun facts, and so it’s a little bit more of a holistic perspective of who you are and we hear from our recruiters that if a recruiter looks at your WayUp profile, your LinkedIn profile, if you even have one, and your resume, they’re significantly more likely to message you, and be interested in your application if they see your WayUp profile.

Liz Wessel [17:08] – First of all, I know this sounds self-serving, but I honestly would say, create a WayUp profile and promote it. Other than that, I think a lot of people don’t apply for that many jobs because some career services offices tell you only apply for two or three jobs. That’s wrong, don’t do that. Apply for a lot more than that. The market unemployment rate, thank goodness, is so down, and therefore, people are really getting hired left and right, especially if you’re technical. Especially if you’re a lot of things. I would say, applying for a bunch of jobs and then really, the advice I give most often for people going into an interview is an acronym I like to call REAF, R-E-A-F. It’s research, show enthusiasm, ask questions, follow up. So research, if you show up to an interview and you show that you know more about the company than the person interviewing you, you will impress them, period, end of story, you will impress them. I remember for my Google internship interview, I read an entire book about Google in like two days, and I came and I was name-dropping the person who, not that I knew them, but I was mentioning the person who made the Google logo, and this and that,

Liz Wessel [18:16] – and I was showing I knew so much and I just lived and breathed the company, and my interviewer was super impressed. Which brings me to E, show enthusiasm, so as much enthusiasm as you might think I have right now in this interview. You are probably engaged with me because I’m showing I actually care about the conversation. If you don’t and you’re playing hard to get, or too cool for school, then no one’s going to find you interesting or engaging. Asking question, and you want to ask good questions when candidates ask me at the end of an interview why did you start WayUp, I literally roll my eyes, I don’t literally, in my head, I roll my eyes. I don’t want to actually be rude, but it’s like if you had just Googled that question, you could find it in every podcast or interview I’ve done. And not to say–

Liz Wessel [18:57] – In anyway that I am saying you should know everything about me, but show that you’re coming with questions that you can’t find on Google with one Google search, so come with thoughtful questions. Things like, “If I were to stand out in this role as a rock star, what would that look like? What are the people who really excel at your company have in common,” et cetera. And then as follow-up, 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.

Craig Cannon [19:27] – Do you mean written, like printed out thank you note, like real, or email?

Liz Wessel [19:32] – It’s interesting. Written will help you stand out way more, however, and you’ll almost get a guarantee that the person’s going to see it because everyone opens a handwritten letter. However, you do want the email or note to get to them before, ideally, for them to submit their feedback. And snail mail is snail mail, so. Maybe if you write one and you give it to the doorman on your way out, that could be interesting if you actually write it after, and by the way, the thank you note should not just be, thank you for your time, it should be, I really enjoyed that we talked about X, Y, and Z, or I really liked the insight that you gave me about ABC, so as specific as it can be, that’s great. But I would say you want them to ideally get it, if possible within 24 hours because then, maybe they’ll get it before they submit feedback about you

Liz Wessel [20:15] – and that might help them, if they’re in between a yes and a no, it might help them lean one way.

Craig Cannon [20:20] – What about the communication skills, because that seems like this whole broad category where even if you apply, your whole model, this REAF model, if you come on too hot, it’s like, “Whoa, this is intense.” Or, if you just can’t communicate quite well enough through your WayUp profile or LinkedIn or whatever. What do you advise someone to do there? Are there books that you tell them to read or how do they handle that?

Liz Wessel [20:45] – I don’t have any books off the top of my head, I’m sure there are some great ones. The most common advice we give is just practice with your friends, specifically the friends or family members who will be honest with you, so not the ones who are yes men or yes women, but the ones who are going to tell you when you suck, and the ones who are going to tell you when you’re being super clear, and you should ideally be practicing with someone who you think is a good communicator, because getting bad advice from a bad communicator is not going to help you get any better.

Craig Cannon [21:12] – I’ve done a handful of interviews in the past on the interviewer side, and that to me can be a little oppressive. it’s like, “I know everything about you, I’ve looked at every single one of your tweets in your whole life.”

Liz Wessel [21:25] – Creepy, creepy.

Craig Cannon [21:26] – Do you guys encounter that kind of thing here?

Liz Wessel [21:29] – Yes, I have had some crazy ones. Like crazy, crazy ones. But sometimes it’s appropriate. As long as they’re not being stalker crazy. For example, someone who was applying to be my assistant, who actually I ended up hiring, and he’s amazing, and his name’s Brandon and you probably met him at some point.

Craig Cannon [21:49] – I did.

Liz Wessel [21:50] – Brandon watched or listened to a couple podcasts of mine before coming in to interview with me, research. He showed tons of enthusiasm, by the way, and asked great questions, and did do a very nice follow-up, but he came and it was so funny, he had this great conversation, it did not feel in anyway like he was creepily stalking me, I didn’t even know about all the podcasts, he just seemed like he really knew his shit, and he seemed like he really wanted the job for the right reasons, it was a very casual, but really pleasant conversation, like the one we’re having right now. That’s the best interview, is one where it feels like a conversation, not an interview. But at the very end he goes, I just want you to know, I think the fact that you wear mismatching socks at all times is hilarious. I know it’s weird I saw that, you mentioned it in the podcast with you and blank, and I really think it’s hilarious, and in honor of that, I’m wearing mismatching socks today, and he shows me, and I just laughed so hard, and I was like, “That is memorable.” I thought it was funny, and it wasn’t creepy, he didn’t have my picture on his socks, that would be like, oh my god, ban this guy from our office.

Liz Wessel [22:55] – But it was funny, it was nice.

Craig Cannon [22:56] – That’s pretty good, yeah I think I would just draw the line at like anything approaching someone’s family or their boyfriend or girlfriend.

Liz Wessel [23:02] – Weird, yeah.

Craig Cannon [23:03] – Like keep that part out.

Liz Wessel [23:05] – Agreed.

Craig Cannon [23:06] – What about like just this whole process of presenting yourself to find a co-founder, how did you go about finding JJ?

Liz Wessel [23:13] – Basically, this is embarrassing. Talk about being a weirdo. In sophomore year, a little bit of a backstory, sophomore year, I had no idea what I wanted to do with my life, like most college kids.

Craig Cannon [23:29] – Standard.

Liz Wessel [23:30] – Freshman year I came into Penn thinking I wanted to be a politician because I had interned for Hillary’s first Presidential campaign in high school, senior year of high school, realized in college that I had interned for one politician and really didn’t like the person and realized that a lot of the politicians I was meeting in that process were pretty scummy people, and I just said, “You know what, maybe I’ll go the Bloomberg route of trying to get into politics one day, once I’ve made an impact on business, but I want to do something where I can be impactful and not surrounded by scumbags.” Fortunately, not all politicians are like that, but a lot are. Freshman year, I’m trying to figure out what I want to study, sophomore year, I start studying actuarial math, computer science, and politics, trying to figure out again. And then I get this email saying Anheuser-Busch is interested in hiring you to be a campus ambassador. And I said, what’s Anheuser-Busch, and what’s a campus ambassador? So I Google both, Anheuser-Busch, cool, I like beer, not their beer as much as I would like, like I love Blue Moon, but that’s fine, I like beer.

Liz Wessel [24:31] – And then campus ambassador, it seemed like it was this marketing job, and I didn’t know what marketing was, I’d never taken a marketing class, I thought marketing was making TV commercials and that’s it. Obviously, it’s much more than that. My first instinct is, I want to get as much experience as possible, and I want to build my resume, and hey also get paid, that’s nice. I took the job, and it turned out that I was being hired to not promote their beer, but to help them recruit mechanical engineering students to work for Anheuser-Busch. I thought that was, A, the first time I realized I loved marketing, and B, the first time I realized that the whole career services/college recruiting process is kind of broken. Now fast forward, my senior year, I knew I wanted to start a project because I’d gotten the offer to Google early, and I ended up taking it by like October or November, so I had the rest of senior year to do whatever I wanted, and I thought why not start a project. Not even a business but as much as a project. I signed up for a Hack-a-Thon, thinking I’m going to create a website that will help college students find campus ambassador jobs, called The Campus Rep. SI sign up for a Hack-a-Thon, and it turns out it’s the same night as, I don’t know, some big party or something.

Liz Wessel [25:48] – And I had to choose between the two, and what I ended up doing was I found my way, snuck my way into, I think in YC, they call it they hacked your way into the database of every single person who signed up, where I could see their resume and all their information. You were not supposed to see any of that information. But, it’s fine, I did. It wasn’t illegal, I don’t think. I went through every line and looked up every single person who signed up for the Hack-a-Thon and there was one that was, by far and away, the most impressive to me, and it was this guy named Joel Fliegelman, Joel, JJ nickname Fliegelman. And I thought, I’ve never heard of this guy, I look him up, we have no mutual friends.

Craig Cannon [26:22] – Why was he impressive?

Liz Wessel [26:23] – A bunch of reasons, he knew how to code, and I know that sounds obvious, but a lot of people who sign up for Hack-a-Thons don’t, he knew how to code, he had done some really interesting projects that he mentioned about like scraping this and this and whatever, he also had a very strong business sense, he was in the Huntsman program, which is a dual degree program between Wharton and basically linguistic studies in the college for what he was studying. He was like Huntsman program, which is really impressive program, plus he knew how to code, and he’d worked on really cool projects, his hobbies were really funny and interesting, I just thought this guy sounds great, I’m going to email him and if he doesn’t respond, cold email him, if he doesn’t respond, I’ll cold email someone else and I’ll go down my list. But he was my first choice, the only one I emailed. I cold emailed him, and I told a little bit of a white lie, which I regret, but I did say, my friends, I thought, your point about creepy stalkers. I thought it would be weird if I said I found my way into the database of the Hack-a-Thon and I’m messaging you, so I said, “My friends told me that you’re a really talented engineer, I’d love to meet with you for a beer at City Taphouse, which is a great bar on campus,” and apparently because he likes that bar, he agreed to meet with me, but he totally knew that I was lying about the friends because in his email back to me, he goes, it’s so interesting that your quote friends, end quote

Liz Wessel [27:41] – told you, because in his head, he was like, I know we don’t have mutual friends who told you this. That was kind of funny. And then we met and I pitched him on the idea and he thought campus ambassador jobs were so interesting, and so he said, let’s do this, and then that obviously turned into something more, and more than just campus ambassador jobs.

Craig Cannon [27:56] – Oh, wild.

Liz Wessel [27:57] – That’s how we met.

Craig Cannon [27:58] – Interesting, okay. Were you curious about vetting him before you got going, as like someone who hadn’t been in engineering school? What’d you do?

Liz Wessel [28:08] – Well, I had taken more coding classes than he had, actually.

Craig Cannon [28:11] – Oh, crazy.

Liz Wessel [28:12] – Interestingly enough. But no, I didn’t think about that. I was like, it’s just a project, I’m not paying the guy. I wasn’t paying the guy, like we were equal co-founders in this thing, if it fails it’s not even like whatever. It’s like we’re both going down. Let’s try it together. Yeah, I didn’t even think about that.

Craig Cannon [28:30] – Really.

Liz Wessel [28:31] – I had a lot of trust in him, still do. I trust him with my life.

Craig Cannon [28:34] – Obviously your co-founder. Now you guys are three and a half years in, you said?

Liz Wessel [28:40] – Just under three and a half, I’d say three years and a few months.

Craig Cannon [28:44] – Okay, so pretty close, yeah. What’s it like now? You’ve been at YC for a couple years. You’re obviously here in New York, how are things going?

Liz Wessel [28:53] – We did YC six months into the business, or five months in, so less than three years ago, it’s crazy, it feels sometimes like a month ago, and it sometimes like ten years ago.

Craig Cannon [29:02] – Interesting, okay.

Liz Wessel [29:04] – It’s going great. I mean, it’s hard. Starting business, everyone always says starting a business is so hard, it’s this roller coaster or emotion, and it’s really easy to hear that and nod your head and say I get it, but it’s so much harder to go through it. But it is the most fun I’ve ever had in my life. I’ve learned more in the past three years than in the entire, I’m 27, so in the 24 years before it, maybe with the exception of the first five years of my life, where I learned the whole English language, but that’s–

Craig Cannon [29:32] – Learning how to walk, all that stuff. We should break that out. Because we’ve done a bunch of podcasts with people who had been in YC, and we’ve done a handful of people who have left YC, obviously. But you’re not that far out, right? What have you learned in the interim, like intervening years?

Liz Wessel [29:50] – I said to Sam Altman right after YC, I was at a lunch or dinner, and he was there, and we were sitting next to each other, and I turned to him and I said, you know the thing that I’ve had to learn about the most since YC, that you guys did not prepare us for at all, and he had a really good reason for why. But that you did not prepare us for at all, was how to manage people and hire a team and grow a team. That is the hardest thing ever. It’s funny and ironic because our business is a recruiting business, It is so hard. I went on Saturday and did a whole talk to a group of 30 entrepreneurs, who were all five employees or less, all about how we came up with our WayUp culture values, and this and that, and they all raised their hands with questions, which each their own like the most challenging questions about employees, having affairs with other, this and this, and I’m just like this, all of this is really difficult. That’s probably the thing I’ve learned about the most, so like scaling an organization, managing people infinitely more senior and experienced than you, hiring those people and convincing them to take pay cuts to come work for you, and so on. I’d say that’s probably the biggest learning.

Craig Cannon [30:59] – We should break that down into like specific examples. Say you’re recruiting her first big senior person. What was that like?

Liz Wessel [31:07] – Okay. The first senior, quote unquote person, he wasn’t C level, but he was like VP level, I worked with a recruiter, and it was really interesting working with a recruiter, because recruiters, the first time you work with a recruiter, they teach you so much about how you should actually hire, they teach you about something called scorecards where, and I’m talking not an internal recruiter, I’m talking an external recruiter who does this for a living, executive recruiters are what they call themselves. They teach you about a thing called a scorecard where you create a set of criteria for any role, of things that they have to be, whether it’s skills or culture, or soft skills, hard skills, and you come up with this entire scorecard, and then you have to rank each person on that. They teach you about the interview process. They help you learn how to sell the candidate. Especially if the person has a kids and a family, which this person did. Coming to a company that at that time, we’d only raised $9 million, which is still–

Craig Cannon [32:07] – It’s a lot of money, but yeah.

Liz Wessel [32:08] – It sounds like a lot, but that’s not enough to ensure that you are going to be around for years and years to come. Technically, no amount of money is. You still have to convince them of that, that’s it worth it for them to risk everything to come to you. It was just a lot of learning.

Craig Cannon [32:25] – How do you sell it? I mean, obviously you’re excited about your company. You kind of sell the vision, you sell the dream, but what are the real, tangible things?

Liz Wessel [32:34] – The biggest one is definitely the person who is going to be managing them, and in my case it’s me, I guess. I have to be selling that I’m going to be a good person that they want to work with, and that I’m not going to micromanage them, that I’m not going to annoy them, and that I’m going to be a really good partner I’m obviously the second thing, as someone once told me, actually a bunch of people have said this to me, people quit their manager before they quit their company, and I’ve seen that very often be true here too. I would say first things first, making sure that you convince them you’re going to be a great partner for them, because no matter what the company does, or what the culture’s like, no one wants to work for an asshole. The second thing I would say is definitely convincing them that the business has legs, and that the business is a great idea that can change the world, or whatever your goal is. For us, it’s very much to help people. That we’ve already had some kind of learning from the first, at that point, we’d been around for a year. That we’ve already had some kind of learning that will help ensure that we have a real shot at becoming a huge business, and the list goes on.

Craig Cannon [33:36] – This is something that I had difficulty with. Managing people whose personality type doesn’t really gel with mine. If you say there are five to ten different kind of personality types, and maybe your personality aligns with like two or three of them, and then there’s the rest. How have you figured out how to manage all those kinds of people? Do you delegate to like other people who gel with them, or what?

Liz Wessel [34:00] – If I’m being honest, if you’re working for me, there’s a few things that you have to have in personality type that I won’t hire you to work for me directly, and it’s fine to work for someone else, but I’m not going to hire you to work not for me, if you don’t, for example, if you don’t consider yourself kind of a little bit Type A where you, we have one of our WayUp principles is “Great isn’t good enough.” If you always strive to just be better than great, to be the best, that’s very much a good thing. I was raised by my parents where if I was in second place, why didn’t you get first? And if you got first place, well that’s expected. If you got a 99, my dad would call and say why do you not think you got a 100? And I know that sounds crazy, but I work best with people who are like that from a standpoint of management. Not everyone at my company is like that, and that’s good, you want that diversity of thought, not just diversity of gender and race and all that stuff, but also of thought. But, from a management perspective, I do like having that hyper competitive and kind of Type A personality. But there are other things, so one person who reports to me is definitely not nearly as, I would say organized, as others, and while that could frustrate some people, I know that kind of lack or organization is totally made up for by that person’s utter creativity. They’re so creative and always coming up with really cool ideas. You just have to balance, and you have to know, I’m going to manage this person to make sure

Liz Wessel [35:25] – that I’m telling them, please follow up with written action items for each of us so that you don’t forget what your action items are, but I understand that you’re probably not going to have as formal an agenda in our calendar invite as other people well, and you just kind of live with it.

Craig Cannon [35:41] – And is JJ the same as you?

Liz Wessel [35:43] – JJ and I are so different.

Craig Cannon [35:47] – Does he have like a different kind of group that he can delegate to or manage?

Liz Wessel [35:50] – He’s definitely Type A too, I will say that. He manages the engineering and I don’t really touch his engineering because I don’t know what I’m doing thee, and the engineers here are so amazing, and I should not be telling any of them what to do. He and I are super different. I’m extremely blunt, and I don’t hold back at all, and he’s a little bit more savvy and tactful, probably with how he gives feedback, if I’m being honest. There’s a few difference that make him much stronger than I am, and some differences that make me stronger. We both have our pros and cons.

Craig Cannon [36:26] – You in other words shave developed this whole company around people that you can manage well.

Liz Wessel [36:33] – That’s just for my management team. There are definitely people here, who I’ve struggled with managing and now they report to someone else and we’re good to go, they report to someone else, and we’re good to go and they’re doing a great job, so I would just say overall, the people who report directly to me, I want to make sure I have a great relationship with them, but there are people at this company who have, if they reported to me, they would be failing, and I would be failing working with them, but that’s okay because they work great with someone else.

Craig Cannon [36:53] – And what else has been difficult for you, aside from managing?

Liz Wessel [36:56] – It’s not even difficult as much–

Craig Cannon [36:58] – It’s like learning.

Liz Wessel [36:58] – It’s a big learning. Other things, focusing on focusing, I know that sounds silly, but you really want to be good at one or two core things, and there are so many shiny objects out there, and it’s specially in our space, our space is super broken. HR tech is pretty behind the times, I mean, we’re sending men and women into space, and yet we’re still really struggling to get applicant tracking system integrations into place, really basic technology issues. What I would say is there are so many opportunities and so many things we want to do, and deciding and prioritizing what you want to do is really hard. The good news is I just hired this awesome VP product who should really be helping me with that, so hopefully that works out, knock on wood.

Craig Cannon [37:45] – Yeah, okay. Because there are, what’s WayUp’s unique insight? Because there are, obviously you have competitors, right? What do you guys do differently?

Liz Wessel [37:55] – We have three components to our platform for candidates. One is a job board, one is candidate sourcing, so profiles, and one is content and advice. The job board is not just, you go to, and if you and I both go, let’s say I’m an amazing engineer, and you and I bot look up engineering jobs on Indeed, we’re going to get the exact same recommendations because you’re probably logged out, et cetera, and I’m probably logged out, they don’t know anything about us. I think that’s crazy. You should not have to scroll through thousands of links, we should be giving you personalized recommendations, based on who you are, what you want, what other people who look like you I want. That look like you from like a standpoint of what school or what year, not physically.

Craig Cannon [38:32] – Right, not literally.

Liz Wessel [38:32] – And the list goes on. Personalized recommendations, candidate sourcing is somewhat similar to LinkedIn, but as I mentioned, we have these amazing profiles that really show who you are in your best light, you are more than your work history. We want to show that, and recruiters can log in and search through people, just like on LinkedIn, for example, and they can message you if they’re interested in speaking to you about a potential job opportunity. That really drives a lot of hires, and then the third aspect is content, advice, have you prepared for this interview? Or, hey we saw that you were looking at this job at Unilever, and we say you didn’t apply, why? Here’s a piece of content about why Unilever’s such an awesome place to work for. And so we have lots of, it’s this integrated approach that we’re really just trying to help as many people figure out what they want to do, and then actually get that job. And so one in three people how apply on WayUp get hired, which we’re really proud about. That really, a few other on each job sites have been able to tout.

Craig Cannon [39:35] – Cool. This is a problem that I’m trying to figure out at YC all the time. What is the most effective content for the most amount of people? In our shoes, it’s getting people to start companies. What has bee the most effective piece of content for you guys, in terms of getting people to apply through WayUp?

Liz Wessel [39:52] – I don’t have a great answer other than unique content that will actually make a company or a job standout as being not something, combat the myths that might misunderstand, so you look at an investment bank on Wall Street, so I was just talking about climate right before this, and they are a classic, Wall Street bank and you look at them and you think they’re probably a bunch of boring white dudes in a room, banking all day.

Craig Cannon [40:20] – Whatever that means.

Liz Wessel [40:22] – From 6:00 am to 2:00 am.

Craig Cannon [40:24] – Staying up late for some reason doing something.

Liz Wessel [40:25] – Yeah, they don’t care about the world, like there’s all these horrible myths about it, and then you actually speak to them and you learn about what they’re doing and you actually realize, yeah some people are exactly like that. But there’s also really cool jobs and really cool opportunities, and so how can we highlight what makes some companies and some jobs really unique for the specific reader, so we try to do a little bit less at scale, and a little bit more targeted content around this piece of content, we hope engineers who also happen to be a diverse, some kind of underrepresented minority, whether it’s female engineers or diverse engineers, et cetera, we’ll read this piece of content. We hope that freshmen will read this type of content, et cetera, and then what we can do with our database is we’ll send it out to the right people who we want to read it.

Craig Cannon [41:11] – Are you doing Facebook ads and stuff like that? Really targeted towards freshman engineers?

Liz Wessel [41:16] – We do some Facebook ads, we don’t do too many, but we definitely has one person who’s paid that much attention.

Craig Cannon [41:23] – Broadly, how do you feel about where education is going? In terms of preparing yourself to be employed or starting a company.

Liz Wessel [41:33] – I love how many companies are no longer obsessed with a college degree, and are now starting to think more about skills. I love how many companies don’t give a shit what your major is, I think that’s really important. I mean, I went into product marketing and had never taken a single marketing class at Penn, or in my life, I still don’t always know what marketing is.

Craig Cannon [41:56] – I was an English major, I have no idea.

Liz Wessel [41:57] – Exactly.

Craig Cannon [41:58] – One time I asked a bunch of people at my company, what do you do and what did you study, and not one of them had studied a single thing related to what they do. The long story short is, I love that people are using their educational experience, I love when I hear that people use their education to learn about things that they love, and not necessarily that thy want to do for a career, because you might be super passionate about chemistry, love studying it, love studying it, love studying oceanography but not actually want to be a scientist or study the oceans. That’s really cool, that the way companies are moving is allowing you to have that channel for studying what you’re passionate about, but not necessarily having to go into that career. Maybe it’s just something you want to study.

Liz Wessel [42:45] – If you’re a small company, say you’re like you just did YC and you’re going to make your first hire, how do you make yourself look attractive to all these fresh, wide-eyed college grads?

Craig Cannon [42:55] – It’s two things, number one, showing why your company is really interesting and special, and usually that’s part of the mission and what you’re accomplishing or what you’re trying to accomplish. Then number two, making it very clear that the team is amazing and that you’re going to be part of the beginning of something really special and huge. People don’t join start ups because of the compensation, that’s for sure. They join because of the team and the mission. I think you have to focus on that.

Liz Wessel [43:23] – Now you’ve been running this company for several yeas now, what do you imagine your life looks like in ten years?

Craig Cannon [43:31] – Ten years is a long time.

Liz Wessel [43:33] – I know.

Craig Cannon [43:34] – It’s like more than a third of my life. Okay, so I can talk about what I will hope I have accomplished by then. It’s super corny, but I’ve always said I want to make a difference the world, and I want to be remembered for making a change for the better, in the world. Not for the worse. I really hope that I’ll have accomplished that in 10 years. 10 years is a really long time, so I hope WayUp will be the thing that helps me accomplish that, and maybe I’ll have done something else by then, who knows.

Liz Wessel [44:07] – How do you think you’ll improved yourself? What are you working on right now to get better at?

Craig Cannon [44:12] – I hope I’ll be a better everything, team member, manager, thinker, product person, marketer, sales person. I’m improving in literally every area at all times, right now I am figuring out how to be better at answering questions for interviews. I hope I’ll get better at everything. And personal-wise, 10 years, for all the women watching, I hope I’ll have a family by then. I’m so glad, if I’m being honest, I have some friends who are founders of really early companies and they have babies or they’re pregnant, I don’t know how they do it. I have a dog, and I’m like constantly forgetting, more like I’m freaking out, like oh my god will I remember to put out food. A human being is a whole nother animal, literally. I hope to have had a child or be married and all that stuff, but professionally, I hope to have had some kind of like really big impact on the world that I’ll be remembered for. My favorite thing, career-wise, I hope I’ll just love whatever I’m doing, my favorite piece of advice I ever got was actually, and I always say this to college students, my college graduation had one of my friend’s dads turn to me and said, people spend their whole lives being so paranoid about making sure they marry the right person, and you spend so much time dating and figuring out who the perfect match is, and they don’t do that with the careers, because I guess it’s a little more taboo to divorce than to switch jobs, but you spend more time with your job and your career than you do with your spouse for the first 40 years

Craig Cannon [45:41] – of your marriage, most likely unless you retire really early, so like really making sure that you find the right job, or a job that’s going to make you happy, so that you’re not miserable every day is equally as important as often it is finding a spouse. If you are so lucky as to be able to have a choice, I would say, for me, I hope I will have a choice and have a job that I love.

Liz Wessel [46:02] – For a college student, someone who was in your shoes, or is in your shoes, how do they find the thing that they really care about?

Craig Cannon [46:09] – Obviously by doing as much as you can by way of part time jobs and internships so you can have tested that out before you go into your first full time job, 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, to try out everything in college. By the way, there’s a really cool site called where they can find it. But I would say, not doing something for the money. I know it’s so attractive to be able to pay back your student loans, but it’s also so attractive to be able to be happy in your job, and you’re going to do such a better job at your job if you’re happy. Doing something that you think you’re going to love and working with people you think will teach you is infinitely the best decision for your first job, and your second and third, and every job after that.

Liz Wessel [46:59] – Totally, I think that’s such great advice. Just get started early and don’t worry about it being perfect, had so many shitty internships that were just like, okay don’t need to do that.

Craig Cannon [47:08] – What was the shittiest?

Liz Wessel [47:09] – It was mostly shitty because I didn’t get paid anything, I was working at an animation studio and that was actually fun. But how I had to make ends meet while living in New York was less fun, like working at night.

Craig Cannon [47:22] – Luckily, that’s usually illegal now.

Liz Wessel [47:24] – Oh, it’s illegal?

Craig Cannon [47:25] – The government’s made it really hard to legally have an unpaid internship. There are ways, but it’s way less common. We have less than nine percent of internships on WayUp are unpaid.

Liz Wessel [47:34] – Oh, wow. I just graduated in 2011, so things have changed.

Craig Cannon [47:38] – Yeah, a lot. I would say the same thing, just get started early and go to school in a city, I would also recommend.

Liz Wessel [47:45] – Yeah, I loved going to school in Philly, but I think you could make both work.

Craig Cannon [47:51] – I was jealous of all my friends who lived on the quad and had all that, but starting in New York at 18 to me was so awesome.

Liz Wessel [48:00] – Cool.

Craig Cannon [48:01] – Cool, well thanks for coming in.

Liz Wessel [48:03] – Yeah, thank you for having me.

Craig Cannon [48:04] – Actually, thanks for hosting.

Liz Wessel [48:06] – You’re welcome.

Craig Cannon [48:07] – All right, thanks for listening. As always, you can find the transcript and the video at, and if you have a second, it would be awesome to give us a rating and review wherever you find your podcasts. See you next time.


  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon