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10 Topics Entrepreneurs and VCs Don't Openly Talk About


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During State of Innovation tomorrow, startup founders will get to ask venture capitalists the tough questions that often go unasked—and vice versa—during the Venture Crossfire Panel.

In preparation for the panel, we also asked readers to throw out some possible topics related to startup funding for discussion. We’ll use some of the best responses for discussion by entrepreneurs and VCs during the panel.

Here are some of the reader responses.

What are the questions that VCs never answer?

  • What's the real reason you didn't invest? Have you ever actually told a team you don't believe in them?
  • How much money does someone really invest into a company if they believe in it? Have you ever invested in a company just for the sake of investing?
  • Have you ever publicly stated (on Twitter or elsewhere) you were a proud investor in a company that was struggling at the time? Investors only say they're proud investors until after things are looking up.
  • In my opinion, VCs shy away from directly answering the questions pertaining to "at what point a company is fundable" or give a generic answer regarding revenue. I believe it's easy to tell entrepreneurs that they are fundable when they are making money but I always wish, with their experience and expertise, VCs would give more direct insights into what can be done to improve a venture's chances.
  • How will my company be compared against others in your portfolio when your partners are making follow-on financing decisions with limited fund reserves?

What are the fundraising topics entrepreneurs never talk about?

  • Do they manage to the business or their exit?
  • How much "creative license" is OK when telling the story of your startup, your metrics, progress and accomplishments?
  • When our fundraising fails. Sometimes it turns into a party round or AngelList syndicate deal or something like that. But nobody will admit they really failed to achieve their goals. We just celebrate the money in the bank as if that's what we wanted all along.
  • Entrepreneurs are focused too much on raising VC/angel money out the gate. Many make the goal of starting a venture to raise capital when the focus should always be on customers. The topic that isn't discussed is how to be successful without VCs.
  • Sharing cap table and terms (preference, dividends, ratchets, control) with prospective recruits when hiring.

The Venture Crossfire panelists are Rudina Seseri, Partner at Fairhaven Capital; Jeff Bussgang, General Partner at Flybridge Capital Partners; Rob Go, Co-founder and Partner at NextView Ventures; Anna Palmer, CEO at Fashion Project; and Nick Rellas, co-founder and CEO at Drizly. The panel will be moderated by Boston Globe tech columnist Scott Kirsner.

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