Create a sense of urgency — and other advice from leading female VCs & entrepreneurs at Stanford GSB

Panelists: Sarah Smith (Bain Capital Ventures), Katherine Boyle (General Catalyst), Kirin Sinha (Illumix), Jooyeon Song (Mani.Me)

Key Takeaways:

• It’s crucial to have a strong perspective on what you’re doing. VCs crave to look at well-reasoned theories of the future so have a sense of conviction on what the world will look like in 10 years. Know why you can’t work on anything else to build that world. You can be wrong on your perspective but be certain; VCs have been wrong before but it’s always because the founder had the conviction that they believed in.
• You have to know your stuff better than anyone has ever known your stuff. If you have thought through every single assumption, you don’t have to pitch — you can sit down and have a Socratic discussion with VCs. Being able to go deep in the first meeting (about your space and product) and high in the second (about sector and TAM) shows extraordinary competency. Build the ability to zoom in and out of your business.
• When doing diligence on VCs, talk to the CEOs of the last 5 failed portfolio companies. There’s always a story, and it’s important to assess how VCs act when things aren’t going great. How partners behave during term-sheet negotiations is also telling of how they will behave when things are bad.
• The most successful deals happen when there’s a sense of urgency / fomo. First-time entrepreneurs sometimes say they’ve started raising and intend to close the round by end of summer. Instead, the more attractive approach is “we started raising last week, have 2 term sheets — we’ll make a decision on Saturday.”
• The difference in pitch styles starts early. Female founders will often reach out to a VC requesting a casual conversation and “advice.” Male founders are often introduced to a VC with urgency and momentum.
• Founders should both always be raising — but also never be raising. There’s nothing more attractive to VCs than “We’re just heads down focused on the product right now.”

Advice for Women:

• Women are supposed to be more numerate than men — you have to know your numbers cold (i.e. what was revenue in Q1 2 years ago?).
• We come from Kardashian culture where media has taught us to up-speak. Unconscious bias around that is real, and this is held against women. If needed, work with a voice coach to speak with more authority.
• Finding an investor is a partnership, spend time getting to know one another. It is never to early to start the conversations because they want to get to know you as a founder as well before making a bet on you. You should be open and honest while maintaining professional boundaries. Stanford GSB has a focus on “touchy-feely” but the real world doesn’t appreciate that same view.

“Contrary to what GSB taught us, no one wants to know or cares about the stories that move you. VCs are just trying to understand what you’re building. They’re assessing to see if you have the subject matter expertise and general entrepreneurial qualities. They’re not really looking to build a relationship with you, that comes with time.”