like they don’t matter. Often times associates can introduce you to the partners before you pitch in a way that sets you up right. And that is really important; it gets the meeting going the right way. Try and meet later in the week. Most partners do their meetings on Monday. We remember the presentations that are earlier in the week better. I don’t know if that is statistically relevant, but there is certainly a better recall on Monday for companies we met later in the week. Don’t over negotiate. Don’t be set in what had in your mind when you walked into that room. Different funds like to do things different ways. It should be open during the conversation. It shows that you can be somebody who the investors can work with. This isn’t about negotiating the single best deal. It is about trying to figure out what is right for the business. What is the right amount to raise to safely get to a series B? Do the founders and rest team have enough equity? Is there an options pool created where you can recruit enough people. Is this the right amount of capital? If you over-negotiate and stick to the one thing you had in mind you will probably lose. Telling a really big but believable story. We are going for huge exits here. We are looking for the companies that will be outliers. We want to think that you’re going for that grand slam, but that you can actually do it. I would rather you give a believable pitch that shows your company can become worth a billion dollars, than an unbelievable pitch for a fifty billion dollar company. Lower the perceived risk any way you can. Venture capitalists are looking for ways to say no. We see roughly 150 deals a month. We say yes to one every six weeks. It is pretty easy sometimes, even if it is not intentional, to say no to companies. It is easier to push them off and focus on the companies that are hitting all the criteria. So look for ways to get risk off the board. Look to get the reasons for saying no off the table. Learn from every meeting you have. When you first start out pitching, pick funds that you think you will be less likely to get because it really trains you better. The more real-world pitches you do the better you become over time. Afterwords have a meeting with your co-founders and learn the feedback from the investors. Adapt the presentation, how you deliver, and you will be better the next time. This is the best free advice and help you will ever get at these meetings. Ask for ideas, referrals, customers, because you will get it. They want to see what happens if they send a customer your way. Have a good time. The companies that produce an enjoyable conversation, a sense of fun or flow, and everyone is happy — in a good mood. Those are the ones we tend to have the longest conversations about on Mondays. Questions: Calacanis— That was amazingly comprehensive and gave me a lot of ideas. What is a company that you said no to and is successful now? Give us some of your anti-portfolio. Katz — A recent one we said no to was Laurel and Wolf. They have since gone on to get tons of customers and raise a successful series B. Laurel and Wolf help get interior designers online and set up things for them. Calacanis— When you look back on that, why did you disqualify them. What did they fail? Katz — There was a lot we liked. They got really close. The product at the time was not good enough. Whether it was our failing or their failing at the time, probably a little bit of both — the conversation did not lead to exactly how the product would adjust and iterate along the way. We really did like the entrepreneur. It was more about the business than the entrepreneur. Calacanis— So the business didn’t work well enough? Katz — The product didn’t. Calacanis— It would be like if you used Uber in the early days and the car didn’t show up? Katz — Right. And then I passed on Kickstarter. They were super early when they pitched us. They went in a much broader direction, but they focused on things like what the city of New York would need to raise money for. Calacanis— They didn’t understand how people would use their tool? Katz — Maybe they did understand, but they didn’t articulate well enough at the time at how broad it could get. These big ones that we passed on are just as much our