How to get people to invest in you

NB: Before we begin: this is the latest article in a series on modern leadership mastery. The series overview and links to previous articles can be found here.

2010: It’s pasta night. Every night is pasta night. It’s delicious and very cheap and healthy enough. I’m living paycheck to pay check. These days, every new client is the difference between making rent, and not. 

Gelman calls. He says, “Hey Jay – a family friend runs a college in DC, and they’re looking for a speaker. I think you’d be a great candidate. I already mentioned you to her and she’s interested in chatting. In a sec I’m going to send an email introducing the two of you. Just wanted to give you a heads up.” 

Several weeks later Gelman’s friend is now my client.

That was five years ago and every time I think about that story, I remain grateful for Gelman’s help. In fact, I still find myself searching for ways to help Gelman and happily go way out of my way to make it happen.

Not once did Gelman ask for anything in return. He helped me just because he could. Because we are friends. Because he wanted to.

The end result: my life was better (I was able to pay rent!) and Gelman has yet another friend who is actively searching for ways to help him. That’s a beautiful thing.

Building a team of people who want you to succeed in three steps

Leaders dream of having an army of people who will enthusiastically respond when called upon for donations, advice, manpower, connections, activism, etc.

Though this is technically called networking, I tend to avoid that term. Using a special term implies that helping one another is something beyond a simple human need and desire. It’s not. At least it’s not if you do it authentically.

All you need to do is follow three rules:

1) Proactively help people when you can

2) Directly ask for help when you need it

3) Don’t worry about keeping score, instead trust that it will all work out in your favor

1: Proactively help people when you can

This is exactly what Gelman did. He didn’t wait until I was begging my friends, he simply saw an opportunity that would benefit me, and spent 15 or 20 minutes making it happen.

That’s the secret. Help people when you can. Be proactive about it.

Think back to a time when someone helped you without being asked. It feels like an amazing gift has been dropped into your lap.

Interestingly, this has the side effect of seriously winning the receiver’s favor. In many cases, the recipient of your generosity will be so charmed by you that they’ll start going out of their way to improve your life.

That’s exactly what happened with Gelman and I. Five years later and I’m still trying to find ways to help him…

2: clearly ask for help when you need it

One of my friends, lets call him, W* has a crush on a lady in my social circle, lets call her J*.

W* knows that I don’t particularly enjoy J*’s company, but that I end up hanging out with her from time to time anyways because we have a lot of mutual friends.

One day, W* said to me, “Hey, I know you don’t like hanging out with J*. Next time you two are together, give me a call and I’ll come save you.”

That felt so slimey. What W* really wanted was for me to set him and J* up. If he had directly asked for that, I would have been delighted. It would have been fun to play matchmaker and see what happens.

But instead, he disguised his intentions and made me feel weird. It made me pause and contemplate whether or not W* was trustworthy. It made me wonder how often he had been less than straightforward with me in the past.

Too often people avoid saying what they actually want. They’re afraid to show themselves, afraid to be rejected, afraid to find out that their desires are unobtainable. And I get it. I struggle to directly ask for help sometimes too. It’s vulnerable. But it’s also really important.

The second rule is this: directly ask for help when you need it.

Clearly and directly asking for help is the key. You’ll be pleasantly surprised to find that many people are happy to help you.

Haven’t you had experiences where a friend asks you to help them move or prepare for a presentation or something and you actually get excited about helping them? I do. It sounds strange, but I love helping my friends load and unload a moving truck.

Understand that your people feel the same levels of excitement when you give them the chance to help you too.

Too many high performing people would risk their lives for the people they love, but are too embarrassed to ask for help when they need it. If that’s you, I urge you to get over this. Work on leaving your comfort zone. It’s in our nature to help people. We can’t truly thrive without accepting other people’s help, but it’s down to you to actually ask for what you need. People can’t read your minds.

3: Don’t worry about keeping score, instead trust that it will all work out in your favor

And here’s the glue that holds the first two rules together: don’t worry about keeping score.

In a society where so much is transactional, it feels normal to use favors as a form of currency.

Bad idea. If you’re helping people just to get them indebted to you, you’ll short circuit the process.

The whole process rests on this: view people (including yourself) as people, not ends to a mean. Realize that you have nearly infinite things in common with everyone else. If you dig just a bit, you’ll notice that you can relate to nearly everyone else at a deep level. Let their success be a win for you. Let your success be a win for them.

If they need ten hours of help, and you give it to them, they don’t owe you ten hours of their time. If you help someone learn how to make Pad Thai, they don’t have to teach you to change your oil.

Just let it rest at this: if you need help, ask. If you can provide help, do.

Realistically, some of your relationships will be unbalanced. If it’s extreme, talk to them. Or say no more often. It’s fine not to help when you can’t.

To keep score is to undermine the process. It’s to make it transactional. It’s to use the other person as a means to an end. It will work in the short run, but not in the long run. If you’re doing something just so someone else will do something for you in return, might as well just pay them or hire a professional. Or be explicit about the relationship you’re setting up.

In every arena that truly counts, you win by investing in other people’s success and allowing them to invest in yours.


Simple homework this month…

  • Ask for help from someone. For some people, this will be simple, you’re used to it. For others, this will take a lot. Regardless, ask someone to help you with something. It can be borrowing a few bucks, helping you bring the groceries in, teaching you to waterski, giving you notes on their one man play, whatever. The goal is to help you understand that asking for what you need is no big deal.
  • Provide help for someone without being asked. Spend time thinking about how you can help someone you care about, and do it. This can be dropping off dinner for a stressed friend, running errands for your mom, or volunteering for the less fortunate. Regardless of what you do, notice how you feel when you do it. Remember that other people feel the same way when they help you.
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4 COMMENTS ON THIS POST To “How to get people to invest in you”

  1. Collier August 6, 2015 at 7:03 pm

    Jason- I enjoyed the blog as usual, it reminded me of a time when a friend told me in this journey of life, when you’re on the stage shining bright…not everyone is in the front row to see you succeed….some are waiting anxiously to see you fail….To succeed you need to ask for help when needed and be willing to give it, expecting nothing in return.

    • Jason August 6, 2015 at 7:36 pm

      Couldn’t have said it better myself. A lot of people believe that success is a scarce resource. It’s not, but helping them understand that often requires making yourself vulnerable so they can start to truly see you (and themselves).

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