This is really simple advice, but I find it remarkably powerful.

Always ask twice.  If you get ignored the first time, or hear a “no”, it never hurts to try again when you’ve made more progress.  It’s amazing how far a little persistence can take you.

As a simple example, take cold emails.  Of course, there are many times when a cold email gets ignored because it’s not something that gets the recipient excited.

But a significant percent of the time, emails just get lost in the shuffle.  There are so many reasons – vacations, sicknesses, back-to-back schedules, etc.  Personally, almost every time I send a cold email and get ignored, I try again.  And surprisingly, my hit rate with email #2 is pretty good – probably at least 25%.

Now, that may sound discouraging, but that’s actually pretty darn good if it’s someone that you really do want to connect with. I’ve found that it’s probably even higher when it’s a phone call, or something a little more personal. 

You don’t want to take this to excess and start to get annoying.  But I think that two “asks” is usually fine.  I don’t fault entrepreneurs at all for asking me twice about investing in their company.  Especially if things changed materially.  I’ve made three seed investments in companies that I explicitly passed on the first time around. 

I bet this is the same for partnerships and many other sales oriented situations.  I’m a big believer in persistence.  And if you think that it gets annoying, at least ask twice.  The worse you can hear is “no”.