Psychology of Raising: Why People Pleasers Raise Less (And How Founders & VCs Can Break The Habit)

What we'll cover:

• VCs are attracted to a founder's conviction
• People Pleasers let their desire to be liked get in the way of unleashing their own beliefs.
• How this plays out for woman and minority founders
• What VCs can do
• What founders can do

Where this came from:

They say that through hardship comes growth. Well this year, I’ve grown. A lot. 

Not just in the usual way—handling all of the startup obstacles that are standard for any founder—but in an internal way: examining behaviors that may have subconsciously sabotaged my goals.

Through this ‘research’ I’ve come to a conclusion: People Pleasers  (of which I am a first-class example) are at a serious disadvantage when raising money from Venture Capitalists. 

This is not to say that People Pleasers lack good ideas or that they are bad at running businesses. It’s not even to say that People Pleasers can't raise money (I’ve raised over $2.1M to date). It’s just that they won’t get funded by VCs as easily as others, unless they do the work. 

Let me explain why (and what founders and VCs can do about it).

When you are a startup founder, especially in the early stages, conviction is your currency. 

Conviction (also known as integrity/belief) is an X-factor that emanates from your words and guides your answers to an investor's inevitable probing. It’s a confidence, that when combined with a reasonable plan, radiates out of you and pulls people in. 

As the anonymous 'Mr Exits' lays out in their Substack article, The Mystery of Fundraising Iniquity:

“A truly unwavering belief in an idea is a stench that is difficult to ignore, particularly to those external to oneself.”

When investors can’t ignore you, you have their attention. It doesn't guarantee an investment, but it does build a reputation. For better or worse, when you act with conviction you are letting the world know that you are not someone to be F’d with. You believe in yourself. Your business. Your goals. 

And as any savvy investor will tell you, it is these qualities that will get you through the hard times. It is the willpower and the grit that you need to succeed. Conviction is attractive.

On the surface, People Pleasers appear to lack conviction. In an attempt to be liked, we often don't say what we are really thinking. Our convictions are there, they are just buried because our physiology values validation over putting ourselves out there. We fear that others won’t like us if we disagree.

Here's what that looks like in a VC pitch situation:

You (the People Pleaser) walk into a room, confident about your path and your startup. You smile, you shake hands, you pull up your presentation and you are ready to begin. You are excited and eager to show the VCs in the room why your company is the one to bet on.

But then—as is their job—the VC challenges you or suggests another way to execute. It stops you in your tracks. You find yourself using language that sounds like backing down or switching to a new course - the VC's new course! It is language that gives the VC's ideas credence over your own.

Why do we do this? Because we want the VC to like us, even if it is not what we would do ourselves. It is so ingrained us, to react this way. Our underlying physiological responses take center stage.

The same thing happens when the VC asks a question that we don’t know the answer to: we fumble and delay. Our minds work overtime trying to guess what the right answer is that will please them. We can’t possibly say that we don’t know or what we truly think! We would run the risk that we won’t be liked. And if we're not liked, we won’t secure an investment. 

Sound stressful yet? It is. 

The mental gymnastics that People Pleasers go through are exhausting. 

Sadly, it also erodes our chance of success.

The flip-flopping nature of People Pleasing has the opposite effect to what we want: it's fundraising repellant. VCs need to trust that founders can make firm decisions, with, or without counsel. Flip-flopping erodes this trust, and without trust, you'll never see funds transferred into your bank account!

How This Plays Out for Women And Minority Founders:

Women are more likely to be People Pleasers than men. As a result, we are also much more likely to subconsciously sabotage the relationship that we need to form with a VC in order to secure funding. What a sobering thought...

It's also my hunch (with no proof as yet) that underrepresented founders are more likely to be People Pleasers in the pitch-room as well. Underrepresented founders often carry the burden of feeling 'less than'.  Add to this the power dynamics of a successful VC who doesn't look or speak like you, and it's a recipe for people pleasing tendencies to come to the fore.

So What Do We Do About It?

Let's recap:

• VCs are attracted to conviction.
• People Pleasers have conviction, but they let their desire to be liked get in the way of unleashing it.
• In an attempt to be liked, People Pleasers will often flip-flop in the pitch room or agree to everything that is suggested.
• This is fundraising repellant because it erodes the VC's trust in the founder's ability to make and stick-to their own decisions, with or without counsel.

What VCs can do:

• Perceive flip-flopping in the pitch room as what it often is: a People Pleasing tendency.

• Determine if the founder shows promise by asking them to think through what they would do and to come back to you with a plan they believe in.

• Assure the founder that it is not what you say that matters: your job is to provide input, not final decision making.

• Recognize, that just as you can help a founder to reign in their ego, you can equally train a founder to unleash their convictions. (Some might even say that the latter is preferable!)

What Founders Can Do:

1. Dig Into Your Past

   • Discover where your own People Pleasing tendencies come from (I'd highly recommend reading How To Do The Work by Dr. Nicole LePera).

2. Build Trust Before You Pitch

   • People Pleasing tendencies often go away when we are speaking with someone who already knows and trust us.

   • Try to form genuine relationships with VCs before you are raising a round of funding. Building trust in a low-pressure way will be of enormous value when you get to the high-pressure pitch.

3. Own Your Convictions

   • Before you pitch, be brutally honest with yourself and write down:

   • Why YOU started your business

   • What YOU would do next to grow it.

   • What YOU anticipate the weaknesses in the business to be and how YOU are going to plug those holes.

   • How YOU are going to respond to investors when they tell you “you should do this instead” or “have you thought about that?”

4. Consider raising through equity crowdfunding instead of VCs

   • It can be much easier to show your convictions when you are messaging a crowd of people who you may never meet or speak with one-on-one. 

5. Don't beat yourself up

   • Don't beat yourself up if your People Pleasing tendencies keep showing up. It is through awareness, attention, and perseverance that you'll begin to see change.

If conviction is indeed an ingredient for a successful VC raise, then it is one of the things that many founders (particularly women)  must work on unleashing. After all, our convictions are what led us to become entrepreneurs. Now we must work on making them heard.