Do (Be) Something Different
Let me ask you a question. If you were applying to a job - which is intrinsically about standing out as optimal for a given role - why would you intentionally sabotage yourself through looking the same as everyone else. In other words, why on earth are you still using a resume? I've been advocating this for nearly two years now. But the problem had never been more apparent when I spent many hours combing through >100 resumes in my duties as a TA for the Chicago Booth PE/VC Lab. Perhaps the problem is compounded at Chicago Booth - where all students are expected to utilize an identical template - but despite a couple of surprise companies or connections here and there people seemed pretty darn similar. That's the way it goes when you attend a school with 1,000 other brilliant people.
And it's why I never voluntarily send resumes anymore. True, you gotta have a resume, applications request them all the time. But in the startup or VC world where so much of your job is outbound, an e-mailed resume, unless specifically requested will very frequently hit the trash.
After a recent trek to Silicon Valley where myself and eight other Booth students met with a variety of VCs, I followed up with below infographic:
An important point is that everyone needs to do something that reflects themselves. My goal was to communicate that I'm planning on staying in Chicago, that I'm not asking for a job, but that I am an expert on all things Startup/VC in the Chicagoland area. And that if I send them a deal in the future, they will know it's not the first thing I've seen. Or if they get invited to Chicago, maybe they'll give me a call.
You need to figure out what your goals are and do something extremely creative that represents yourself. That doesn't mean a 15 page research report, nor does it mean a 15 minute video. Do something simple - one pager. Pique interest. If your goals are a job, prove you're an expert in an area that matters to them. If your goals are a relationship, prove you're worthy of a 30 minute coffee. These principles apply both to in-demand VC jobs and in-demand startup jobs.