Caveat: This post is not about cyber security but I think it’s a fun story that some readers might appreciate.

Chris Sacca

Chris Sacca is the most successful seed investor of all time. Sacca himself was several million in debt a decade or so ago (due to bad bets in the stock market) however now Forbes estimates his net worth at over $1 billion, due to early investments in companies like Twitter, and Instagram. That number is due to expand as more of his investments exit, notably Uber, Stripe and Lookout.

Venture funds would be happy to invest in any one of these companies, but Sacca has invested in unicorns time and time again. Needless to say I wanted to work for him. The problem was, Sacca’s fund, “Lowercase Capital” (pun very much intended), doesn’t really hire. Unlike Insight and Bessemer who come to Penn’s campus every recruiting season, Lowercase is just a three-person team. I had to figure out an angle. How could I pitch myself? Luckily the answer to that question practically slapped me in the face.

I was listening to a recent interview with Sacca in which Sacca was describing how he picked companies. Sacca explained that because the pace of seed investing had quickened, he now had to judge a lot of his investment decisions based off of his initial impressions of the founders. He didn’t have an analyst digging into their companies and industries. That was the bait I needed! I immediately sent him an email explaining that as an analyst performing due diligence, I could help him get a more complete picture of the companies and founders he was thinking about investing in.

A Shot in the Dark

The email was a shot in the dark—I didn’t expect a response—however the next day, he responded, asking me what I could do to add value to Lowercase. I set up an emergency meeting with my entrepreneurship professor and I called all of my friends who had worked in venture capital to get their advice. I sent him back an email several hours later with my thoughts. And then I waited. Several days. No response. Had I just squandered my opportunity to work with the most successful seed investor of all time?

I decided that a simple email wasn’t enough. Anyone could do that and it didn’t show much initiative. I scrolled back through his tweets and noticed that he had tweeted out a link to a website created by someone who pitched AirBnB on how they could add value if they were an AirBnB employee. I would do the same thing for Lowercase, highlighting what Lowercase needed and why I was uniquely suited for the role.

Another Chance?

I stayed up until 4:30 Friday night trying to put something together on Wix. The next day I went to the library and disregarded my stat homework to work on the website. The Lowercase website had a Wild West theme. I decided to recreate this for my site. Chris was serious about not taking himself too seriously and I tried to recreate this vibe on my site as well. Here’s the finished product and I’ve included a sample of the site below.

So did it work? As of the time of me writing this post, two days after sending the site out, no. However I’m optimistic that he’ll at least take a look and I’m keeping my fingers crossed. The great thing about this is that you, the reader, have the chance to help me create a happy ending.

If you think he should take a look, throw me a retweet on Twitter, @foodieatfifteen or tweet @sacca mentioning http://www.nickandlowercase.com/ . Thanks so much for reading!