Liz Wessel, the 28-year-old CEO of Millennial job-hunting startup WayUp, clearly knows a few shortcuts to success. Before she's even passed her 30th birthday, Wessel has started a successful college business, worked at Google, and founded a booming company with 50 employees, $27.5 million in funding, and 3.5 million users.

In a recent in-depth chat with Y Combinator, Wessel shared one of her top tricks for cutting ahead in your career journey. It's dead simple in principle but tricky to get right in practice: Cold email your business heroes.

Wessel started her cold emailing career early and wasn't shy about aiming high right out of the gate. When she was finishing college and weighing whether to take a job at Google or a venture capital firm (yes, she is clearly an achiever), she managed to email Roelof Botha of top VC firm Sequoia to ask for advice. (He said go to Google. She did.)

Cold emailing is a bold move Wessel suggests to other ambitious young people, but it's important to do it right. What does that entail? She offered a ton of detailed advice.

  1. To get email addresses, try tech plus guesswork. "I have Rapportive on my computer, which is this software that LinkedIn bought [and rebranded as Sales Navigator]. 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," Wessel explains. "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.com ... and then I'd guess like roelofb@sequoia.com, rbotha@sequoia.com, 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."

  2. Go with a catchy subject line. Big names get a ton of email. You have to stand out, and a generic line about wanting to "pick someone's brain" isn't going to work. "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," Wessel coyly relates (she's probably talking about Sheryl Sandberg). "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. I actually 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, you're going to open the email."  

  3. Leverage your youth. Very few bigwigs can say no to a hopeful young achiever asking for advice. "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," Wessel advises students.

  4. Be short, direct, and well informed. Then "get to the point. What do you want help with? And ... why are you asking him or her?" instructs Wessel. "Show somewhere in there that you've done your research and that you're not just trying to email famous people."

  5. Don't ask for a phone call. Haven't you heard that no one likes the phone anymore? And that's extra true of insanely busy superstars. "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 a.m. and stops at 1 a.m. almost every day, five to six days a week, and so for me, 20 minutes on a calendar is actually a really big deal. Sending me an email that I can just answer on my walk from one meeting to another is not," Wessel explains.

Follow these five bits of advice and "you'll probably get a good response rate," Wessel claims, even if you aim high and cold email some of the biggest names in business. Want more wisdom from this ambitious young founder? Check out the complete interview below.

Published on: Jun 7, 2018