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

At what point did you know you wanted to start a company?

Um, so my sophomore year of college, I was at Penn, and I actually started my first business at the end of sophomore year. I went to Stanford for a three-day boot camp called Basis Entrepreneurial Boot Camp or something like that. I remember going to the Jamba Juice at Stanford, and they asked me, "Can I see your Stanford ID?" I said, "I don't have one. Why?" And 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."

So, I get back to campus, and I walk around to all the restaurants, and I say, "Do you have any loyalty program for students?" And they all said no. So 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. I said, "Okay, I'm not gonna pay you for that or anything, and I'm actually gonna charge students," and they were like, "Okay, we don't care."

I ended up over sophomore summer, and I also was doing an internship at Blackstone in Tokyo, but meanwhile, I hired a company in China to create thousands of cards that would put the logos of all these businesses on the back. I called it the Penn Eats Card, and I got back to campus at my junior summer. I hired all my friends to basically go around selling these cards for 15 bucks a pop, and we sold thousands. It was awesome, and it was very, very cool. That kind of gave me the bug. I was addicted. I thought the concept of creating something from nothing and solving a problem or, you know, helping people is just such a cool opportunity, and why wouldn't you want to do that over and over?

Because you weren't an engineer, right?

You're right. No, I took a bunch of computer science classes, but I was not what I would call an engineer.

And so, were you inherently drawn to creating a software startup, or did you like try out other ideas?

At first, it was like a Wix website and a bunch of plastic cards, not really much software. The 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 be a software bazaar, you know, an internet company.

Okay, but you didn't start it immediately after school.

So the story was WayUp, the high level, is my senior year. I'm happy 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. 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, and of course, all good backpackers do, went to McKinsey in New York. 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.

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." If you build a website that you barely do any marketing work for, and it’s grown that much, then we knew that we had something. So, we shut down that website because it was just like a kind of half-ass project. But we took the insights from that and built WayUp off of that.

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, you know, like financially they have enough flexibility to leave, just kind of get in this cycle like oh, you know, they get a raise every six months or whatever and they stay there forever.

Yeah, oh man, Google is a cushy job. It's an awesome job. Great, yes, hard, but really awesome.

Okay, so I always wanted to start a company full-time after college, but my senior year, I applied for—so I had 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. For me, I had got enough advice, and I’d started that Penn Eats company and saw that there was so much I had to learn, whether it was managing people, legal documents, like marketing, sales, and so forth. So for me, I basically said I want one experience that will help me before I start, you know, before I start whatever company I one day started.

I did not know it was gonna be WayUp, or that it would be web. I said I really want to do it for two years, whatever this job is. I'm gonna learn as much as possible for two years, and then I'm gonna quit, and I'm gonna 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 gonna leave this job in two years. I’d start a company. Is that okay?

Google's so cool. I mean they especially—the program I was applying for, and I got the offer to, is called the APMM program, Associate Product Marketing Manager job. The whole program is filled with alumni. They hired like 25 to 50 of us 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 + Co, and the list goes on. Some former Googlers—Robby Stein started a really cool company called Stamps, sold out to Yahoo.

So, long story short, all of these people were in this program, and 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 had many successful founders as well, one who just recently had his company go public. So I couldn’t choose.

I did what I always tell college students they should do, which is cold emails someone who they want the advice from. So Roelof Botha was someone who I had seen speak at the Stanford Basis Entrepreneurial Boot Camp. It's all going kind of full circle. So at the end of the day, I email Roelof Botha and I say, "You are, you know, one of the best venture capitalists in the world. You’ve seen—you’re 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 X Y Z fund or start my own or go to Google in this program?" And he said, "I would get the best possible operating experience I could get, and 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, so go Google."

Good, I've heard you talk about this on a couple of other podcasts!

I love cold email.

Yeah, me too, actually. I am one of the people I really admired in San Francisco when I was still living in New York. I cold emailed him, Skyped him, and I was like, "Oh man, it's just so weird. I'm gonna be in San Francisco like next week. Are you gonna be around?" He's like, "Yeah, I'll be around!" And then I just bought a flight.

The best! If you could afford to do that, that’s the best. Entrepreneurs do that a lot, apparently, to get like venture capital meetings. I thought that was funny.

It totally works.

So say you’re—you don't have a brand name or whatever, you're just a college student just like you. Can you walk us through the steps that you use to cold-email?

Hmm, totally. So 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 figure out someone's email if you can't find it already online by basically guessing. So, 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 Sequoia’s comp. My guess is Charles at Sequoia.com. Arbol both that Sequoia, and I keep guessing until his image shows up on the right in Rapportive, and that’s when you know you got the right person.

So sometimes if they're big enough name, you can find their email address online, but if they're not, then that's the best way to do it. So once you have that, I would say the subject line has to be something that's going to catch their attention. So wanting to pick your brain from a college student is not gonna stand out. Any college student can do that. My best 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 gonna say her name and you can guess, and my subject line—I saw that she had taught like aerobics or done aerobics in high school or college or something, and I had taught water aerobics the summer between high school and college ’cause they pay a lot of money.

Oh, alright, so who knew?

Okay, so I actually wrote in my email, and I think part of the subject line, like, “Fellow former water aerobics”—like something silly—but it caught her attention because if you see something ridiculous that someone clearly had to do a lot of research to find out about, they’re gonna open the email.

In the email, I wrote, "Dear blank," and I start off with, "I'm a college student at blank." You know, 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, you know, 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. So use it and abuse it while you're in college.

Yeah, but I mean 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, so they only start with like “I’m a college student at X school,” yeah, and then they get to the point. What do you want help with? Ideally, show that you’ve done your research, so why are you asking me? So you know, in a specific case for Roelof, I remember I said something to the tune of like, “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, right?”

So I do think that a very big part of your email should be saying why you are asking this person. What do you want from them? Who are you? Then show somewhere in there that you’ve done your research and that you're not just trying to email like famous people.

Mhm, um, I think if you do those things, you’ll probably get a good response rate. We did a podcast with Casey 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.

Exactly! Sometimes I get people asking me about hopping on a phone call, and I know it sounds so crazy, but literally my calendar starts at 8 a.m. and stops at 1 a.m. almost every day, 5-6 days a week, and so for me, 20 minutes on the calendar is actually a really big deal. Asking me in email that I can just answer on my walk from, you know, one meeting to another is not.

To diverge a little bit, you talked about your calendar. I read online that you don’t sleep a lot. Is that true still?

Yeah, okay, so how much do you sleep?

Okay, 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. So if I have any sip of alcohol, I do sleep. If I have like a glass of wine, I will fall fast asleep, or a beer or anything. But assuming I don’t drink, which is most nights, I can go 3 or 4 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.

So your whole life you’ve been like this?

Yeah, I mean, in high school, I remember my friend Laura came to me one day and was like, "I have a Hanukkah gift for you." I said, "What?" She was like, "I'm gonna be your assistant, 'cause I feel like you never sleep, and you have such a crazy agenda. I'm gonna calendar, and I just want to help you." I was just like, "I don't need an assistant, but thank you." I think I've always had a crazy calendar.

That's wild! So, given that crazy schedule, do you have any particular health regimens you need to stay normal?

People are gonna 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—um, 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 or Uber if I want to call and I need quiet.

But I eat pretty healthy. I'm not like a—I don’t like sweets much, so yeah, I'm not uncopyable tomorrow. People who do yoga every day—and by the way, I don’t judge people who do yoga. A lot of my friends do yoga. I'm just not like a—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.

Walking is very good for you.

Yeah, yeah, I drink a lot of water. If you sit down with me at a meal, you will hate me because I will ask for two pitchers of water, 'cause I will drink water the entire time when I'm not talking.

We should have more!

Sorry!

Alright, so more of the tip stuff. What are the most common questions you get when you are getting these cold emails from college students, and what tips do they ask for?

For internships, 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, yeah, like the real-life story.

I get a lot of people asking for advice when they're student entrepreneurs starting a company, and I think that’s amazing. I mean, when I started my business in college, I would say I was one of like five people I knew who had starting companies, and now I feel like it's a prerequisite just graduating from college in the US, 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, so I think that's another one I get a lot.

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?

It's very specific, and often I respond saying like you need to give me more context here because 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 8 things you have to do before you graduate or whatever. 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.

I think it's nice that he tried to keep it short and sweet, but I could only do so much, okay? What do I know? You know, yeah, one opinion.

Yeah, what about on the actual application side? 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, you know, probably the right qualifications for it?

We really do. It’s wayup.com/guide or wayup.com/blog. We have a ton of content—like thousands of verticals. What I will say is number one—and this is not meant 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, your YouTube if you are a performer or a public speaker, your Instagram if you're a designer. They show you are a volunteer, your hobbies, your fun facts, and so it's a little bit more of a holistic perspective of who you are. We hear from our recruiters that if a perk reader looks at your web profile, your LinkedIn profile—if you even have one—and your resume, they're like significantly more likely to message you and be interested in your application if they see your WayUp profile.

Okay, so 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 sub Career Service offices tell you to only apply for two or three jobs. That's wrong. Don't do that! I applied 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. You know, especially if you're a lot of things. So I would say applying for a bunch of jobs, and then really the feedback, the advice I’d give most often for people going into an interview is an acronym I like to call REAF.

Okay, so 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. And the story—you will impress them. I remember for my Google internship interview, I read in a book about Google in like two days, and I came, and I was name-dropping the person who—not that I knew them, but like I was mentioning, you know, the person who made the Google logo and this and that, 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 like hard to get or too-cool-for-school, then no one's gonna find you interesting or engaging.

Asking questions—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, I in my head roll my eyes. I don’t actually be rude, but it’s like if you just Googled that question, you could find it in every podcast or interview I’ve done. Not to say in any way that I’m 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? Etc. And then “F,” follow-up. Just send a thank-you note. No one, especially college students, tend to do this these days, and it makes you stand out so much. It shows this level of professionalism, which really is pretty easy to accomplish by just sending a thank-you note.

Do you mean written? Like to like print it out, thank-you note like real?

It’s interesting. A handwritten note will help you stand out way more. However, and you’ll almost get a guarantee that the person’s gonna see it because everyone opens their, you know, or handwritten letter. However, you do want the email or the note to get to them before, ideally before they 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 thing, you know, it should not just be “thank you for your time.” It should be like, “I really enjoyed that we talked about XY and Z,” or “I really like 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, and that might help them if they're in between a yes and no.

So what about the communication skills? Because that seems like this whole broad category where even if you apply your whole model, like this REAF model, if you come on too hot, it’s like “Whoa, okay, this is intense,” or if you just can’t communicate quite well enough through your WayUp profile or LinkedIn or whatever.

Would you advise someone to do their—are there like books that you tell them to read, or like how do they handle that?

I don’t have any books off the top of my head. I'm sure there are some great ones. I think the most common, you know, 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 gonna help you get any better.

Okay, yeah, ’cause 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 like drought. Like, do you guys encounter that kind of thing here?

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. So, for example, someone who is applying to be my assistant who actually ended up hiring, and he's amazing and his name’s Brandon. You probably met him at some point, and Brandon watched or listened to a couple of podcasts of mine before coming into interview with me. He researched, he showed tons of enthusiasm, by the way, and asked great questions, and ended to a road, and I followed up.

But he came, and it's so funny. He had this great conversation. It did not feel in any way like he was creepily stalking me. I didn’t even know about all the podcasts. He just seemed like he really knew his, 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. And that's the best interview: one where it feels like a conversation.

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.” And I know it’s weird—I saw that, but you mentioned it in the podcast with you and Blanc, yeah—and I really think it’s hilarious, and in honor of that, I’m wearing mismatching socks tonight. He shows me, and I just laughed so hard. I was like, “That is memorable! 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, BAM! This guy from our—” but it was funny.

That’s pretty good. Yeah, I think I would just draw the line at anything approaching someone's family or their boyfriend or girlfriend.

Yeah, we're good. I keep fart out!

What about like just this whole process of presenting yourself to find a co-founder? How did you go about finding JJ?

So basically, this is embarrassing; talk about Viggo weird up. Okay, so I in sophomore year—a little bit of a back story—sophomore year I had no idea what I wanted to do with my life, but like most, you know, college standard freshman year, I came into Penn thinking I want to be a politician because I had interned for Hillary’s first presidential campaign in high school, senior year of high school. I realized, at my time in college, that I had interned for one politician and really didn’t like the person, and realized that a lot of the other politicians I was meeting in that process were pretty scum—pretty scummy people.

I just said, "You know what? Maybe I’ll go the Bloomberg route of trying to get into politics one day once I have like made an impact on business, but I want to do something where I can be impactful and not surrounded by scumbags." So, fortunately—not all politicians are like that, but a lot are.

So 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. Then I get this email saying Anheuser-Busch is interested in hiring you to be a campus ambassador, and I said, "What does Anheuser-Busch and what's the campus ambassador?" So I Google both. Anheuser-Busch, cool, I like beer—not their beer as much as I would like. I love Blue Moon, but that's fine; I really, you know, I like beer. 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. And you know, obviously, much more than that. So my first instinct is I want to get as much experience as possible, and I want to build my resume, and hey, I also get paid—that’s nice. So 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, and I thought that was—the first time I realized I loved marketing, and be the first time I realized that the whole career services/campus recruiting process is kind of broken.

So now fast forward my senior year, I knew I wanted to start a project, 'cause I got in the offer to Google early, and I ended up taking it by like October or November, so I kind of had the rest of senior year to do whatever I wanted. I thought, “Why not start a project?” Not even a business, but as much as a project. So I signed up for a hackathon thinking I’m going to create a website that will help college students find campus ambassador jobs called the Campus Rep.

So I sign up for a hackathon, and it turns out it's the same night as, I don’t know, some like date party or something. Okay? And I had to choose between the two, and what I ended up doing was I found my way, stuck my way into, I think, NYC—they would call it, they’d have to 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 supposed to see any mention, but it’s fine; I did. It wasn’t illegal, I don’t think.

And so I went through every line and looked up every single person who signed up for the hackathon, and there was one that was by far and away the most impressive to me, and it was this guy named Joel Sleek—oh man, Joel J. J. J. nicknamed Legoman. I thought, "I’ve never heard of this guy, look him up. We have like no mutual friends." And why was he impressive? A bunch of reasons—they knew how to code. I know that sounds obvious, but a lot of people who sign up for hackathons don’t.

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 in the Huntsman program, which is a really impressive program, plus he knew how to code, and he'd worked on really cool projects; his hobbies were really funny. I just thought, "This guy sounds great, I'm gonna email him, and if he doesn’t respond, cold email him. If he doesn’t respond, cold email someone else. 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. I said my friends told me that you’re like really talented engineer. I’d love to meet with you for a beer at City Tap House, which is a great bar on campus. 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 ‘friends’ told you, because it is—how’d he—he was like, 'I know we don’t have mutual friends, who told you this?'" So 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." That obviously turned into something more and more than just campus ambassador jobs—so that's how we met.

Interesting! Okay, and so were you curious about vetting him before you got going? Because like as someone who hadn’t been, you know, in engineering school, like what did you do?

Yeah, well, I had taken more coding classes than he had actually. I’m crazy, interestingly enough, but no, I was like, it’s just a pride—I’m not paying the guy. I wasn’t paying the guy. Like we were equal co-founders in this thing. Exactly if it fails, David, whatever—it's like we're both going down, so I thought, "Let’s try together."

Yeah, I didn’t even think about that. I had a lot of trust in him.

Mhm, I still do.

Yeah, I mean obviously our co-founder, right?

So now you— you guys are three and a half years in, you said, just under three and a half?

I'd say three months—three years in a few months.

Okay, so pretty close.

Yeah.

Alright, what's it like now? Having, you know, you've been at YC for a couple of years, you're obviously here in New York. How are things going?

So we did YC six months into the business, or five months in—so less than three years ago. Ah, that’s crazy!

It feels sometimes like a month ago and sometimes like 10 years!

Oh, interesting.

Yeah, so it's going great. I mean it's hard starting a business. Everyone always says starting a business is so hard. It’s this rollercoaster of 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, and 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 real earnings every because we've done a bunch of podcasts with people who have been in YC and we've done a handful of people who have left YC, obviously, but you're not that far out, right?

So what have you learned in the interim, like intervening years?

You know, I said to Sam Altman right after YC—I was at like 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 mean so hard.

I went on Sunday or Saturday and did a whole talk to a group of like 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 hand with questions, each their own, like the most challenging questions about employees having, you know, affairs with others, and this, and this, and I’m just like, “Oh my god, 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. So I’d say that’s probably the biggest learning.

We should break that down into like specific examples. So, you know, say you're like you're recruiting your first big senior person. What was that like?

Okay, and the first senior quote-unquote person—he wasn't c-level, 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 or what they call themselves.

So they teach you about a thing called a scorecard where you create a set of a criteria for any role—of things that they have to be able to have, whether skills or culture, or you know, 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.

I mean especially if the person has kids and a family, which this person did, coming to a company that at that time we’d only raised nine million dollars, which is a lot of money, but I was 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. I mean, no amount of money is. So you still have to convince them of that, you know, that it's worth it for them to risk their everything to come to you.

So, it was just a lot of learnings.

How do you sell it? I mean, obviously, you know you're excited about your company and you kind of like sell the vision, you sell the dream, but like what are the real tangible things?

I think 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 gonna micromanage them, that I'm not going to annoy them, and then I'm gonna be a really good partner.

Obviously, the second thing—'cause 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 so very often be true here too. So I would say first things first, making sure that you know you convince them that you're gonna 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—

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, and that we’ve already had some kind of learning from the first—the point we’ve 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.

What about, this is something that I had difficulty with, like managing people whose personality type doesn’t really gel with mine. I find, you know, if you say, "They're like five to ten different kinds of personality types," and maybe your personality aligned just 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?

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. 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, if you don’t consider yourself kind of a little bit type-A where you—we have one of our web principles that’s great as it—good enough if you always strive to just be better than great, to be the best, that's very much a good thing. So 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 you don’t 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 every one of my companies is like that, and that’s good; you want that diversity of thought, not just diversity of gender and race and all that, 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. 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 that kind of somewhat lack of organization is totally made up for by that person's utter creativity. I mean, they’re so creative and always coming up with really cool ideas, so you just have to balance, and you have to know: I'm going to manage this person to make sure that, you know, 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 the, you know, that you’re probably not going to have as formal an agenda and our calendar invite as other people, well, and you just kind of live with it.

And, is JJ the same as you, JJ?

Oh my god, so DJ is a different kind of group that he can delegate to or manage. He’s definitely type-A, I will say that, but he, yeah, he manages engineering and I don’t really touch his engineering because I don’t know what I’m doing there, and then our engineers here are so amazing, and I should not be telling any of them what to do, so he and I are super different.

I think a lot of people—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 are a few differences that make him much stronger than I and then some differences that make me stronger, you know, we both have our pros and cons.

Okay, so you, in other words, have kind of developed this whole company around people that you can manage well.

That's just for my management team. I know there are definitely people here who I’ve struggled with managing, and now 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 if they were 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, and what else has been difficult for you aside from managing?

Other things? 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. Especially in our space, our space is super broken—like 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 like 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 of product who should really help with that, so hopefully that works out. Not gonna jinx it!

Okay, because there are—what's a unique insight? Because there are obviously competitors, right? Like what do you guys do differently?

So 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. So the job board is not just, you know, you go to Indeed.com, and if you and I both go, let’s say I’m an amazing engineer, and you and I both look up engineering jobs on Indeed, we’re gonna get the exact same recommendations 'cause you’re probably logged out, etc., and I'm probably logged out. They don’t know anything about us—I think that’s crazy! Like 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 want it look like you from like a standpoint of what school or what your—is, and the list goes on!

I’m so 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, you know, LinkedIn, for example, and they can message you if they’re interested in speaking to you about a potential job opportunity, so that really drives a lot of hires.

Then the third aspect is brand is content advice. Have you prepared for this interview? Or hey, we saw that you were looking at this job at, you know, Unilever, and we saw you didn’t apply—why? Here is a piece of content about why Unilever is such an awesome place to work for! So, we have lots of it!

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. One in three people who apply on WayUp get hired, which we’re really proud about. Very few other, if any, job sites have been able to tell.

Cool! This is a problem that I’m trying to figure out at YC all the time, like what is the most effective content for the most amount of people? And in our shoes, it’s like getting people to start companies, right?

So what has been the most effective piece of content for you guys in terms of getting people to apply through WayUp?

I think often—I don’t have a great answer, other than like unique content that will actually make a company or a job stand out as being, you know, not something—they combat the myths that they might misunderstand. So, you look at an investment being on Wall Street. So I was just talking to—right before this, and they are a classic Wall Street bulge bracket bank.

You look at them and you think they’re probably a bunch of boring white dudes in a room banking all day, 6 a.m. to 2 a.m., I played for some reason doing something. Yeah, they don’t care about the world. There are 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 some people are exactly like that, but there are also really, really cool jobs and really cool opportunities.

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 skill content and a little bit more targeted content around this piece of content. We hope engineers who also happen to be diverse, you know, some kind of underrepresented minority, whether it’s female engineers or diverse engineers, etc., will read this piece of content.

We hope that freshmen will read this type of content, etc., and then what we can do with our databases, we’ll send it out to the right people who we want to read it.

And are you doing like Facebook ads and stuff like that, really targeted towards freshmen engineers?

We do some Facebook Ads. We don’t do too many, but we definitely have one person who’s—

Okay, got you.

So broadly, how do you feel about where education is going in terms of preparing yourself to be employed or starting a company?

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 damn 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. I was an English major! I have no idea. 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. So I think 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 they want to do for a career because you might be super passionate about chemistry, love studying it, love studying oceanography, but not actually want to be a scientist or study the oceans. I think that that's really cool that the way companies are moving is allowing you to have that kind of channel for studying what you're passionate about and not necessarily having to go into that career.

Maybe it's just something you want to study.

Okay, and if you’re a small company, say you just did YC and you're gonna make your first hire, how do you make yourself look attractive to all these, you know, fresh, like wide-eyed college grads?

I think it’s two things. Number one, showing why your company is really interesting and special, and usually, that's part of just the mission and what you're accomplishing or what you're trying to accomplish. And then number two, making it very clear that the team is amazing and that you are going to be part of the beginning of something really special and huge.

People don’t join startups because of the compensation, that’s for sure, like they join because of the team and the mission, and I think you have to focus on that.

Mhm, so now you’ve been running this company for several years now. What do you imagine your life looks like in ten years?

Ten years is a long time!

I know! It’s like more than a third of—

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 in the world and I want to be remembered for making a change for the better.

So, I really hope that I’ll have accomplished that in ten years. Ten years is a really long time, so I hope WayUp will be the thing that helps me accomplish that. And, you know, maybe I’ll have done something else by then, who knows?

How do you think you'll have improved yourself? Like what are you working on right now to get better at?

I hope I'll be a better everything—team member, manager, thinker, product person, marketer, sales person. I mean, I’m improving in literally every area at all times. Right now I am figuring out how to be better at answering questions or interviews, so I hope I’ll get better at everything.

And then personally—like ten years, you know, 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 I have babies or they're pregnant. I don’t know how they do it. I mean, I have a dog, and I'm like constantly like, “Oh, I should say forget it!” I was like, “I’m freaking out about that!”

Oh my god! Well, I remember to put up food like a human being is a whole nother animal—literally! So I hope to have had a child and or more, and you know, 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, one of my friend's dads turned to me and said, "You know, people spend their whole lives being so paranoid about making sure that they marry the right person, and you spend so much time dating and figuring out who the perfect match is—the soulmate—and they don’t do that with their careers because I guess it’s a little more taboo to be divorced than it is to switch jobs.

But you spend more time with your job, in your career, than you do with your spouse for the first 40 years 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 gonna make you happy so that you're not miserable every day is equally as important as often it is finding a spouse. So if you are so lucky as to be able to have a choice, I would say, you know, for me, I hope I’ll be able to have a choice and have a job that I love.

Mhm, and so for, yeah for a college student like someone who was in your shoes or is in your shoes, how do they find the thing that they really care about?

I mean, obviously doing as much as you can by way of part-time job, an internship 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 is, you know, um, it’s often because they just never had an opportunity to try it out in college to like try out everything in college, and by the way, there’s a really cool site called WayUp that they can find it.

But I would say, you know, not doing something for the money. I mean, 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 at your job, and you're gonna do such a better job at your if you're happy.

So I think doing something that you think you’re gonna love and working with people who you think will teach you is infinitely the best decision for your first job and your second and your third and every job.

I think that's such great advice! Like just get started early and don't worry about it being perfect. I had so many shitty internships that were just like, "Oh, okay, don't need—" Yes! It was mostly shitty 'cause I didn't get paid anything. I was working in an animation studio, and that was actually fun, yeah.

But how I had to make ends meet while living in New York was less fun—like working now, and like the government's made it really hard to legally have an unpaid internship. So there are ways, but it's way less common. We have less than 9% of internships on WayUp or unpaid.

Oh wow! I just graduated in 2011, so things have changed.

Yeah, yeah, so I would say the same thing—just get started early and go to school in a city!

Yeah, I would also recommend.

Oh really?

Yeah!

Yeah, I mean, I loved going to school in Philly, but I think—yeah, I think you can make both work. I was jealous of all my friends who lived on like the quad and had all of that, but like starting in New York at 18 to me was so awesome!

Yeah!

So, yeah, anyway, cool! Well, thanks for coming in!

Yeah, thank you for having me! Or actually, thanks for hosting!