The Tricky Business of Asking for Help


I’m starting to appreciate an interesting paradox that comes with launching and running a startup, which is this:

You must rely on everyone and no one.

What do I mean by that? Well, starting up anything from scratch can be a monumental task, especially for one or even two people. Some of the early groundwork can be laid on one’s own in front of the computer or with pencil and paper. But more commonly, and in my experience, if you are committed to getting something off the ground and out of side-project territory, you will be reaching out to almost everyone you know and asking for help in one form or another.

It might be getting feedback on early prototypes and business plans, advice on company formation, introductions, providing links for people to share on Facebook and Twitter, asking for someone’s hard-earned money as a customer or investor, or even just reading a two-minute email.

These requests go out to family, close friends, acquaintances, former colleagues and quite often total strangers. Willingness to reach out is actually a good test of your own commitment to the idea; if it’s not something you’re proud of and feel strongly about, you‘ll be hesitant to share what you are doing or ask for anyone’s time and attention.

Looking back at the five months I’ve spent building Level, it’s hard to imagine where it would be without an incredible amount of support, encouragement, generosity and direct assistance from a great number of people. I am truly grateful.

Herein lies the paradox.

You will need to rely on all of these people to move your ideas and plans forward, but the one thing you cannot do is rely on any one for help.

The truth is that no matter how much or how nicely you ask, not everyone will come through in the ways you hope. It took me a little while to learn this. In one particular case, a friend had such direct and specific experience with something I was undertaking that in my mind, getting the leg up I was looking for was just a matter of arranging coffee or connecting on the phone for ten minutes. In pursuing her help and assuming it would be there, I put on hold a number of alternative approaches and tasks. After repeated vague and non-committal responses, I finally realized that for whatever reason she was clearly not interested in engaging.

I took this personally at first. But soon it dawned on me that I had no idea what was going in her life at that moment, and that by dwelling on it I was only slowing myself down. Most people (especially in the startup community) genuinely like assisting others, but sometimes it’s just a matter of timing whether or not they will be able to lend a hand.

Here are a few other things I’ve learned about asking for help:

  • Cast a wide net when you can. Some people will respond immediately and others will not. It usually averages out in the end.
  • Where possible, be very specific with your ask and any action items. Include links, bullet points, anything that helps you get to the point about what you are looking for without others having to figure it out.
  • Sometimes, only a phone call or in-person meeting will do. Learn when you need to go that route.
  • For ongoing endeavors, find a way to keep certain people in the loop without any strings attached. This can be a monthly email update or blog post that you point them to. The chances for serendipitous help are maximized when people have a mental picture of the journey you are on and can connect dots on their own when they come across relevant people or ideas.
  • Avoid making any type of quid pro quo requests. You don’t want to feel like you are taking more than you are giving, but in my opinion the best thing to do is take the general outlook of being helpful where and when you can as a way to pay it forward. Like everyone else, there will be times when you cannot help someone, but when you can, jump at the chance.
  • The more help you get, the more motivated you become to help others.

The sum of all this is that you will need lots of help in building a startup. But don’t wait on any one piece of assistance before moving forward. Reach out for it, follow up, be persistent, but be ready to move on and solve the problem a different way if you need to. And always take time to be grateful.

Thanks to all those who have helped, and even to those who were unable.

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