Reflections on the early days at Zendesk (part 2)

This is part two of my post about the early days at Zendesk. The first part is here.

Small, fragmented and no potential for differentiation

As mentioned in the first part of this post, the seed round was only $500,000 and it was clear that we’d need much more money soon. That’s why Mikkel and I started to work on a pitch deck and a financial plan almost immediately after the closing of the seed round and started to pitch to VCs shortly thereafter.
In my personal experience as a founder, raising money has never been easy, and so I didn’t expect that it would be easy. I was quite optimistic though, since I thought we had a pretty good pitch: a well-rounded team of three complementary and experienced founders, a beautiful product, a proven business model, paying customers and nice (yet early) traction.

So why did all European VCs pass? I’m getting asked this question a lot and I don’t have a perfect answer, but here are a few important factors:

• There just weren’t (and still aren’t) that many VCs in Europe who can write a Series A check. If a couple of them pass for whatever reason, you’ve quickly exhausted your available options.
• Our timing was horrible – it was almost at the height of the global financial crisis which had started in 2007. While we were trying to raise the Series A, Lehman Brothers imploded and a collapse of the entire global financial markets seemed possible.
• We had failed to convince investors that we were going after a large market and that we could build a defensible position. One feedback that we got was that the market for help desk software is “small and fragmented” and that there are concerns about the “potential for differentiation” and several other VCs were concerned about the size of the opportunity and our ability to differentiate, too.

You’ll notice that I haven’t mentioned the “European VCs are risk-averse/dumb/whatever” theme to explain why we haven’t been able to raise money in Europe. While I do think that there are differences between how VCs work in Europe vs. the US, I think it wouldn’t be fair to blame European investors for missing Zendesk: With hindsight Zendesk looks like a clear winner, but back in 2008 it wasn’t that clear. It was still very early.

At a critical juncture

A few months later, after having talked to a number of US investors and and after an almost-deal with a West Coast VC which was pulled back at the last minute, we eventually got an offer from CRV in Boston. We were relieved, but the valuation was much lower than what we had hoped for.

Because of the dilution which the investment round would mean and because the whole fundraising process has been so hard, Morten and Alexander got more and more doubts if going the VC route was the right thing to do at all. They were wondering if we couldn’t go the 37signals way instead – stay a smaller team, grow organically and maybe raise money at a later point in time when we’d be in a stronger position and when the market conditions would be more favorable. That was definitely a viable alternative and worth considering, but Mikkel and I strongly believed that we had to raise money and that we shouldn’t wait. This led to a lot of long emails and Skype discussions between the four of us. It also led to some very heated discussions between Mikkel, Morten and Alexander, which is no surprise, given how much was at stake. We were at a critical juncture.

One relic from those days is this email snippet (Alex in red, me in green):

I still need to buy Alex a T-Shirt with “I’m not confident that Zendesk can grow into a $100 million company” on it.

In the end we decided to take the investment from CRV, but we took a smaller amount than what Devdutt had offered us to reduce the dilution. It was still a significant hit in terms of dilution, but given how many doors the CRV investment has opened for us and how much Devdutt has done for the company it proved to be the right decision.

The rest is history – get Mikkel’s book to read about it!