The Story Behind My Sixth Investment, HelloSign / HelloFax

In setting up my fund, the most stressful aspect was not what you think it might have been — it wasn’t raising the money or talking to LPs, or setting up the legal structures (which are creative, and will discuss later), or trying to jam into good deals. The part of all of this that nearly killed me was the paperwork involved. My brain freezes when given paperwork. With this fund, there was so much of it, I just stayed up one whole night over a weekend and got it done. Late that night, I finally gave in to the fact that in order to handle this paperwork, I’d have to hire an assistant or sign-up for one of the online signature services. “Oh well,” I thought, let’s just sign up for HelloSign.

I had heard of HelloSign when it was HelloFax. I had a friend who worked there and loved it. And, it seemed to solve a real but mundane problem — while the world is now digital, many big industries and government agencies required or still demanded physical paper and fax machines. HelloFax was a reincarnation of online faxing, but now with mobile devices and a new generation in place, the fax machine just has to go. At the time, I didn’t think much of it. Then, I started using the product to finalize the fund, and then more and more, and then I started to tell people in different companies about it, and everyone wanted that solution.

Turns out, I am not the only one. They keep their stats private (the investors know them though), but there are a public few places where you get a sense of how they’re doing. For instance, just from their Google integrations alone, they have over 400,000 users.

I emailed Joel, my friend who worked there, on May 8: “I’d love to invest in HelloSign. Your product rocks.” I just searched GMail for the thread, and 54 messages later, he’d introduced me to the CEO, Joseph Walla, and we talked on the phone a bit and met for lunch. I told Joseph how I started my fund and what I was trying to do, and he did some reference checks. During our lunch, I realized that I wouldn’t be of much help to the team because Joseph had the execution under control, and when I asked him about the more long-term vision, he had a terrific answer — the paperless office. Everything paper will convert to “Hello.”

I was sold there. Now, I just had to convince him to let me participate. Truth be told, I don’t think the company needs me or my investment, but Joseph graciously made room for me, perhaps on the belief that at some point, I could be helpful, because he thought I was being entrepreneurial. That type of gesture means a lot to me, and I hope when the time arrives, I can deliver for Joseph, Neal, and the entire team.