VCs generally get excited about backing entrepreneurs that have already successfully exited a venture. However, the stereotype of the repeat entrepreneur brings with it a concern.

Good VCs expect repeat entrepreneurs to act as partners, as they do everyone else. However, first time entrepreneurs or entrepreneurs that have failed in prior endeavors are known for being more receptive to feedback and willing to engage in a healthy exchange of ideas.  Repeat successful entrepreneurs are expected to be more stubborn, because they haven't yet experienced a humbling business endeavor.

As a result, repeat successful entrepreneurs should make sure to show VCs that they are team players. The best way to do this is by being friendly in the meeting and by being receptive to feedback.  If you immediately dismiss a VCs reaction to your business plan, they'll assume that you'll dismiss them as board members in the future.

VCs are sensitive to this issue.  So go the extra mile to demonstrate that this won't be a problem and it will be even easier for you to get the deal done.

Comments

[Jonathan Treiber]

This is a very interesting take Mark. My belief was that VCs almost always want to work with established and successful entrepreneurs, especially if they've worked with them in the past.

One thought I've always had was the issue of investing in "hungry" entrepreneurs. First-timers or guys who didn't find success with their last venture will tend to be a hungry bunch, eager to work 100 hours a week to make the venture fly. I've met a lot of successful entrepreneurs who don't have that drive anymore after cashing out from their first venture with $50 million. What's your take.