Closed mouths don't get fed. That's definitely true. But a simple open mouth is not that effective either… especially in fundraising.

So what else do you need to know?

First let’s dive into the difficulty of asking for help.

Not asking for help: a common and harmful problem

This is a challenge many entrepreneurs have, especially ones with certain characteristics that I happen to relate to.

Any of these sound familiar?

• The unaggressive type 
• The builders 
• The introvert
• The children of immigrants

Many founders who fit those archetypes (and others) tell themselves certain damaging stories.  They tell themselves they shouldn’t inconvenience people and/or make waves.  They tell themselves they need to prove that they’re worthy and that they can do it all on their own.

Whatever the reason is that you tend to not speak up, learning how to ask for help is a skill you’ll have to develop.

Good advice, but not enough

I love the general advice that everyone needs to speak up. You need to ask for help. 

This is advice that I give quite regularly.  At the same time, an open mouth on its own doesn't get fed. 

Here's where an additional piece of advice can benefit everyone, regardless of whether you're comfortable asking for help or allergic to requesting favors​​. 

Put yourself in their shoes.

What do I mean by that? 

The importance of understanding psychology

First, a story: 

A few months ago, I caught up with my old co-founder Dave who at the time was the co-founder of a popular social app called Gas. This was an exciting time for the company and before Discord acquired them. 

I was fascinated by the overall journey which was full of twists and turns. He shared some crazy stories about conspiracies to spread rumors against their company. There were multiple times where they had to rebrand the app because a group was pushing the lie that they were a front for a human trafficking organization. So wild!

When the dramatic storytelling came to an end, I asked him what he thought made his co-founder Nikita Bier special. After all, Nikita had built and sold a similar app 6 years prior so he had some sort of edge.

Nikita is obviously a smart guy, but what Dave highlighted was how in tune Nikita was to the psychology of his users.  He deeply understood the psyche of high schoolers and used that to expertly design every step of the product experience. Nikita would deftly anticipate what would go through the mind of their users, what emotions they'd feel at every step, and what motivations they’d have to engage. This deep understanding allowed him to build an incredibly addictive and beloved experience that took the high school scene by storm. 

When I heard this description of Nikita and Gas’s special sauce, I immediately thought of my own ability to help founders think through fundraising strategy.  I can pick apart what steps a founder needs to take and how they should communicate with investors, because I deeply understand the psychology of the people they’re trying to influence. I was an investor so I know how they think.

Asking for help? Be like Nikita

Just like Nikita deeply considers what a high schooler might be thinking, you should also consider the psyche of the people you’re asking for help from. If you can put yourself in their shoes, you’ll undoubtedly be more effective in your requests for help.

Who are the people that you’re asking for help from? What is their motivation to provide the help that you requested? What would motivate them to put a lot of effort into delivering on your ask?

When you think about the person you're asking for help from, especially within a fundraising context, the mere fact that they can provide any help usually indicates that this person is influential and likely doesn't have tons of free time. Their full-time job is not to support and provide help for you. AND they most likely won’t directly benefit monetarily from helping you. So what is it?? 

The worst reason someone might help: GUILT

The first and worst reason someone might deliver the help you request is guilt… or more accurately, removal of annoyance.

In other words, you made the ask and they have no other reason to to perform the task other than they feel bad and they want to get rid of you. Now, when I say it’s the “worst reason” I just mean in comparison to other reasons. Getting help for this reason is still a positive outcome and certainly better than not getting help. That said, there are better ways to get help and you should be focused on those. 

For some requests, not all help is created equal

You might be thinking, well if I got the help I needed then what’s the difference? 

This is true if the request has zero nuance to it.  For example, if the request is “Can I get a copy of a report that you have?” it doesn’t matter if the person helping you was super annoyed when they sent it over to you or if they delivered with warm and positivity. You still get the same report.

But what if the request is “Can you make an introduction to Julia Lipton from Awesome People Ventures?” because Julia is an investor that you would love to have on your cap table? 

Well then the difference between someone begrudgingly making an introduction to Julia and someone lovingly and excitedly making an introduction to Julia could be the difference between convincing her to invest and not getting a meeting with her at all.

How to be more successful with your asks

Now that you see how different requests can be, here are a few approaches to making your requests for help more successful. 

Be personal 

No one wants to feel like they are one of a thousand people that were bothered to be milked for a specific value. Even if you are asking multiple people the same thing, do what you can to have a customized approach that makes each person feel like a human rather than a number in a numbers game. Simple human consideration and a personal touch can go a long way.

Leverage reciprocity

Reciprocity is a powerful element of psychology that impacts many situations. When someone receives something they feel obligated to respond in kind. At a softer level, helping first shows you care.

Either way, if you can find a way to help someone first or deliver value, they will be predisposed to helping you afterwards. If you want to become really good at this, spend 5-10 minutes before any call thinking through and researching who this person is, what their business is, and ways you could possibly help. Then spend the call learning more about them to inform your initial research. Asking them what they are most most focused on today can help you uncover the best way to assist them and make your own requests for help be more warmly received. 

Side note: notice I didn’t say you should ask them “how can I help?” That is my least favorite question ever… here’s my essay on why that is.

Relationships first, then asks

Realize that successful asks come off the back of real relationships. What that means is it's best to do what you can to build a relationship before you make an ask. 

Some might say they KNOW they should’ve built a relationship but right now they don’t have time. Just know that this advice can be applied to a micro interaction or an extended period of time. 

For example, if you know you’ll need to make an ask on a first call, taking genuine interest in the person at the start and doing what you can to make the engagement positive before making your ask. 

Or maybe you take the whole meeting to learn about them and find ways to help without making an ask, knowing that you may follow up shortly after with an ask.  Both are great examples of focusing on the relationship first even with limited time.

No matter how much time you have, you’ll never go wrong if you focus on the relationship first.

Don’t be cynical

I realize that breaking down asks like this can make relationships feel very transactional. That’s not my intent.

In general, I subscribe to the idea of connecting with people and wanting to help first, knowing that good things will come around when you’re a good person as opposed to calculating every engagement to extract the most value. 

Going deeper into why things work helps uncover the first principles that drive the systems in play which helps everyone be more creative – especially those of you who have to start unlearning some of the ineffective ways you’ve been asking for help in the past!

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