Jenny Lefcourt is general partner at Freestyle Capital, a venture capital firm that specializes in seed and early-stage investments. She knows what it takes to be an entrepreneur because she’s been there. Lefcourt has sold two companies she co-founded — WeddingChannel.com and Bella Pictures — after dropping out of Stanford Business School. Meetings with investors to pitch the business and raise capital left her with a deeper understanding of the process, and she took that experience with her to Freestyle, which mentors the 12 companies it invests in each year. Its current portfolio includes Wag, the dog-sitting website, Digit, an automatic savings startup and Patreon, which lets fans become patrons of artists, musicians, writers and other creative people.
Leftcourt spoke to Knowledge@Wharton to offer specific and tested advice for budding entrepreneurs. The following are five takeaways from the conversation. (Listen to the full podcast using the player at the top of this page.)
Do Your Homework
Before the first meeting with a potential investor, the entrepreneur should be able to sharply define the company’s business model and have the right team in place. That means doing the required homework and answering important questions: Is this a lifestyle business? Is it a cash-producing business? What’s the short-term vision? What’s the long-term goal? Could the business be worth $1 billion someday?
Lefcourt shared the story of an entrepreneur who “bootstrapped” his idea for months because he wanted to make sure the demand for it was real before he went in search of investors. Once he was satisfied that his idea was solid, he figured out how much he needed and whom to approach for capital.
“There are probably 300 different seed funds, so understanding which one is right for you is the homework you’ll start to do by hearing about reputation, by looking on their website, seeing their portfolio,” Lefcourt said. “If there’s something [in their portfolio of investments that’s] directly competitive, you don’t want to pitch them. However, if there’s something that’s similar, and you think, ‘Wow, they’ll really get it,’ then that is someone you want to pitch. So that’s the type of homework you want to begin to do before you even enter into their office.”
Many budding entrepreneurs make the mistake of information overload. They come to that first investor meeting armed with every possible fact, and they want to share all of it to show how well-prepared they are.
“What’s really important is to not go into the weeds of all the details because what you’re trying to do is give them enough information that they want more information,” Lefcourt advises. “Your goal at meeting No. 1 is to get people interested enough that they want meeting No. 2.”
However, entrepreneurs will need to demonstrate their knowledge of the marketplace, explain what is changing that makes the opportunity exist, and show that they have the right team with the right solution to the problem.
That’s where metrics come in. “You’re really trying to paint the big vision but also provide as much data or as much traction as you can so that not only do they see the vision, but they can believe it can be made,” she said.
It Always Costs More Than You Think
One of the most difficult early tasks for entrepreneurs is figuring out exactly how much cash is needed to move to the next level. Lefcourt has some simple advice on that point: “I always tell entrepreneurs to make sure that you budget for longer and more money, more resources because everything is harder and takes more time than you ever imagine it will.”
But don’t sweat it. She said smart venture capitalists are flexible about funding and can help the entrepreneur figure it out along the way. Freestyle has often recommended more or less capital to the companies it has worked with, for example.
“Your goal at meeting No. 1 is to get people interested enough that they want meeting No. 2.”
“You should know a little bit about what you’re going to achieve, and by when, and the capital you think it will take,” she said. “But beyond that, in terms of what you’re asking the person on the other side of the table, I don’t think you need to worry about that as much.”
Learn to Enjoy the Process
Lefcourt empathizes with entrepreneurs who would rather get back to business then sell themselves in an investor meeting. But that’s the only way to get the necessary financial backing, so they might as well embrace it.
“You have to remember that while your business is what you think about 24/7, you’ve got these people for a half an hour to an hour. It’s your job to grab their attention and be a good listener as well as a good visionary — and paint them a picture that’s exciting,” she said. “You don’t think of venture-pitching as sales, but you are. You’re selling to them that this is something they want to be a part of.”
When it comes to leaning in, attitude is everything. Investors feed off positive energy and people who can handle tough questions and criticism with panache.
“Understand there are really smart people out there, and they’re going to give you their ideas. They’re going to disagree with you,” Lefcourt said. “The more you embrace that process and the more you enjoy that process, the stronger you’re going to be, whether that VC ends up investing in you or not.”
Talk It Out
All entrepreneurs looking to scale up need to find the delicate balance between giving in to get the money and holding the line on what they feel strongly about. Disagreements are common, and the best way to work through them is to communicate.
“Everything is harder and takes more time than you ever imagine it will.”
“There is that line you have to walk when you’re pitching,” she said. “You don’t want to just please them and agree with them, but you also need to be open-minded and thoughtful because people will give you good ideas. The answer as to how to do that is just to be authentic about it, and then you won’t be confused. Know what you feel strongly about and be open-minded to someone pointing something out that could be interesting.”
Lefcourt said she got the best advice in entrepreneurship while working on her first company. She was having a disagreement with a VC, so she went to an independent board member for help. He told her to “sit down and have a nice conversation.”
“The good news is that once someone has invested in your company, everyone is aligned. Everyone wants the company to be successful. Everyone wants the founder to be successful,” she said. “If there’s a disagreement, it should just be discussed — the pros, the cons, the various outcomes. The VC may be right. The founder may be right. There may be something in between. But there’s only one way to get there, and that’s with really open, honest communication.”