Shyp Raises $50m: Some Inside Baseball Notes

Obviously thrilled that Shyp raised a $50m B Round from Kleiner Perkins. As we noted on the Homebrew blog, this is a company with so much growth ahead of them, it’s great to put capital to work. Here’s some more detail on the round, our involvement and what I think it generally means for startups.

• Pro Rata. We remained enthusiastic supporters in this financing, making Shyp the first investment in our Moonshine fund. Moonshine is allocated to pro rata in primarily the B and C rounds of companies from our core funds, when we believe there’s still venture-scale returns to be had for an additional dollar invested.
• Boards. Satya and I strongly believe in the value of Boards at the seed stage because they help founders build cadence heading into the A round. When Homebrew lead Shyp’s seed in 2013, I joined their Board. When Sherpa lead the A in 2014, Scott Stanford was added and has been a huge asset. Now with Kleiner’s John Doerr stepping into a Board role, I’m able to step off into an Observer role. Homebrew’s model is to be partners of conviction for your first few years but we also think founders should not be overwhelmed by VC opinions or control. So we’ll typically step off boards come B rounds.
• Google network rolls deep. I’d met John Doerr a few times while at Google/YouTube because of his role on their Board but that wasn’t the only Google-tie in this deal. Kleiner’s Megan Quinn was one of the early champions for Shyp within their firm. Prior to Kleiner (and a leadership role at Square), Megan held a variety of roles at Google. It’s always fun to bring familiar faces back around the table just in a different context.
• Breaching the Gates. Shyp didn’t run an exhaustive financing process but instead ended up speaking with just a small number of firms who had built relationships with them over time. It was very impressive to see how Kleiner and some other name brand firms did a good job of working with Shyp’s CEO Kevin Gibbon, building trust and proving value. Over time I’ve seen some VCs wait to be told a company was raising. Over time I’ve seen some VCs offer help but do very little proactively (at least until that company is in their portfolio). And over time I’ve seen some VCs get excited but then hesitate at the last minute when it comes for them to stand up in front of their partnership and pull the trigger. Not here.

So if you haven’t tried Shyp yet, here’s a free first shipment (up to $30). They’re currently live in SF, NYC and MIA with a beta in LA. They’re also hiring.

Want more of me? I blog at www.hunterwalk.com & tweet @hunterwalk