Prescient words from Drew Houston in 2008: "Is there a limit to how much a bank account can hold?"

By Sarah Lacy , written on February 25, 2014

From The News Desk

Yesterday, Pando alum Erin Griffith broke the news that Dropbox has raised an astounding $325 million in new funding. The drumbeat of anticipation of a Dropbox IPO grows by the month -- particularly since rival has filed and is expected to go public this summer.

For years now, Dropbox has made growth look almost annoyingly easy. At its last round, it was one of the first companies to make the $1 billion valuation club look like chump change, and in September 2012, Y Combinator's Paul Graham wrote a blog post explaining that of the many hundreds of companies that have passed through Y Combinator's classes, just two-- Dropbox and Airbnb -- make up 75 percent of the accelerator's overall value. It could likely be the first mega Y Combinator IPO.

In hindsight, the company looks like a no-brainer to start and a no-brainer to fund, and that's how a lot of press describes Dropbox. But, as always with startups, that's not the case.

Dropbox was a painful struggle in the early days that even Y Combinator's Paul Graham didn't have much time for. Here are four snippets from our PandoMonthly interview with Dropbox co-founder Drew Houston that remind you how much this "do no wrong Valley darling" struggled to even exist to begin with.

First, Houston talks about hounding Graham, and how easily Y Combinator almost missed this "black swan." Lesson: Don't take no for an answer or, in Houston's words, spend "ten minutes of being that jackass who wouldn't leave him alone."

Second, he describes his struggles to find a co-founder and the darkest early days of the company. Again, it was a requirement to make it into Y Combinator, and for a few years Houston was essentially begging people to start this company with him.

Once Dropbox made it through Y Combinator, things were easier. But Houston -- like many entrepreneurs -- still felt that he was in over his head. One of my favorite stories was from his awkward first meeting with a smirking, poker-faced Sequoia Capital mega-investor Mike Moritz... at his apartment.

And -- one of my favorite stories from the evening -- even when Dropbox got that first round of cash, Houston didn't quite know what to do with it.

It should be comforting to every entrepreneur who has that moment of deer-in-the-headlight, I-don't-know-how-to-do-this-shit panic: Almost no one does in the beginning. The best just learn by doing, hounding investors, and occasionally asking dumb questions.