An investor in Uber, Duo Security and Spotify, New York-based Green just closed a new $950 million fund from an extensive LP base.
What product or service are you totally, even irrationally, loyal to?
I am incredibly loyal to Followup.cc. I probably use it hundreds of times per week. The software allows you to send an email using a particular protocol to a mailbox, which will boomerang it back to you to remind you when things need to be done. The service allows me to not let things fall through the cracks. For instance, if I ask someone in the office to complete a particular analysis by two days from now, I will also bcc email@example.com. Magically, two days later, the email will boomerang back to me, and I won’t forget to follow up to make sure the task is done.
What’s one startup or product that failed or was shut down that you wish were still here today?
I must say AskJeeves.com. I really liked the interface and used it back in the day. Google is awesome, but in its heyday, AskJeeves was pretty awesome! I think some incarnation of it might still exist, but not like it was years ago!
What’s your favorite piece of advice to give to first-time founders?
First, write handwritten thank you notes to people who help you. Everyone is inundated with hundreds of emails daily. But how many pieces of legitimate snail mail do you get? I don’t think I get more than a few per week. If you write a handwritten thank you note, people remember it.
Second, managing a business is all about setting expectations. Ultimately, as you grow, your ability to forecast future progress and deliver on promises is a very important part of building trust with all constituencies (employees, investors, partners, customers, etc.). I’ve seen companies that set absurdly high targets (whether promising a customer an unrealistic deliverable, or setting an annual budget that is unreasonable). I have also seen companies that sandbag in the opposite direction, which sometimes results in not pushing hard enough. The best companies, however, are the ones that can accurately forecast, which builds credibility with all relevant parties and helps create a culture of simply doing what you said you would.
What do you think is the most significant change happening in venture capital right now?
The unbelievable pace/rapid acceleration of adoption of software in businesses of all sizes is staggering. Software is creating more efficiency across all businesses and allowing corporations to gain insights that were incredibly difficult before. We’ve seen growth in the use of software in everything from a local restaurant to the world’s largest organizations.
What’s the strangest way you’ve ever been pitched? And did it work?
I will flip the question and tell you a funny story about how we once pitched a company to take our money. The company we were chasing told us that they didn’t want a term sheet because of some internal reasons. But nevertheless, we were quite keen on investing. Instead of bringing a term sheet to our meeting with them, we showed up at their office with a Publishers Clearing House-style oversized check. I think the management team all fell off their chairs when we presented them with it. Funny thing is that it worked! We ended up making a large investment into the company, which earned us an excellent return.