Hundreds--perhaps thousands--of entrepreneurs have sat down across the table from Union Square Ventures founder Fred Wilson to ask for money. Most have failed. Those who have succeeded--including Rob Kalin of Etsy, David Karp or Tumblr, and Ben Milne of Dwolla--obviously did a few things right.
In a candid conversation with TechCrunch founder Michael Arrington, Wilson, the founder of one of New York City's most prolific VC firms, offered a few tips to start-up founders looking to raise early capital.
Step 1: Make a bold or audacious statement to open the meeting. Wilson says the best pitches open with a "hook and reel 'em in" method. For example, Jeff Lawson, the founder of Twilio, walked in to a meeting with Wilson and announced: "I'm taking the entire world of telephony and reduced it to five API calls." Wilson was floored. "I said, 'No way, I couldn't believe that.' So hook the person, and then real them in."
Step 2: Don't go through your back story. It's great that your business idea was inspired by growing up on the coast of Maine and going lobster fishing with your grandfather--but Fred Wilson just doesn't care. "Going through a long back story is a bad idea," Wilson says. Get right to the heart of the business idea, and why Wilson should care about it.
Step 3: Condense your entire presentation to one slide. If you're like most entrepreneurs raising cash, you've probably spent weeks building and perfecting your investment deck, which is probably between 20 to 40 slides. That's great, but Wilson says it's a trap, because you end up rushing through the presentation and overwhelming investors with information. Keep it as simple as possible.
Step 4: Show the product, then tell them about it. Too many entrepreneurs get in front of Wilson and talk about the product for 20 to 30 minutes, and only then actually show it. What if you don't have the product yet? Well, best of luck: "We made a bunch of investments in companies that didn't have a product, some worked, but more often than not those are our least performing," Wilson says.
Step 5: Don't let Wilson push you around. When Fred Wilson first met with David Karp of Tumblr, Wilson asked Karp if Tumblr should have a section for comments. Wilson persisted, but Karp ultimately said no, arguing, "comments suck!" At that point, Wilson realized Karp may be on to something. "I stopped arguing with him," Wilson recalls. "The best entrepreneurs will listen to you, but they won't take orders from you."
Step 6: It's OK to be a little crazy. But don't be a pyschopath. According to Fred Wilson, the best foudners are, well, a little bit off. Founders who are a little bit crazy can "see things differently than other people see them and have the courage to act on ideas." But there's a fine line. "I think crazy is a compliment...but you don't want a psychopath."