It's very easy to think of an ask as a negative--of a burden on someone.
When it comes to startups, however, especially when you've built up a great reputation and done a lot of good work for others, people are not only eager to help you, but they take great pride in being asked. Working with you is an opportunity. Getting a chance to take a leap with you is an opportunity. Earning equity in your endeavor, or having the opportunity to buy some of it on the ground floor, is an opportunity. It's a gift and you have to start thinking of it as one.
So, not only does that mean not being afraid to ask, but it also means realizing that if you don't ask, people can feel left behind. We join the startup world because we want to work with the best people. We want to work with innovators and those on the services side of the business--the lawyers, recruiters, and even investors, because I do think investors should be servers, want to be that first call.
When I raised my first fund, I send out a note to a bunch of people whoes input and experience I valued--people I would have been thrilled to work with. I didn't know if they were fund investors or not and I didn't want to put them in an awkward position by making a direct ask--so I just bcc'd them all. I said, "I assume you're not fund investors... but if you are and you want to be involved, I'd love to work with you. The last thing I want is anyone who I admire wondering whether I didn't value them enough to make the ask."
I'll be doing that again for my upcoming second fund as well. I don't expect many to respond, but if I truly think of my fund as an opportunity, it's important for me to know that I would have wanted to work with them.