Try this hack to 10x your fundraising instincts and confidence

October 25, 2022

Here’s a comforting thought for you all: you know more about fundraising than you think.

This might sound strange for me to say given my newsletter’s growth is dependent on founders thinking the opposite, but it’s true. Before I unlock your hidden fundraising abilities “Matrix Style”

Let’s talk about the evolution of founder fundraising education:

It used to be brutal

Fundraising knowledge used to be trapped, hidden away, and overall impossible for most founders to access.  The expertise only existed in the minds of a select few and the only way to transfer it was via 1:1 interactions.  And could you get to those select few easily? Of course not.

It’s gotten WAY better

Now, the combination of new platforms / media to share information plus VCs excitement for content marketing has unlocked access to this expertise. Between Twitter, podcasts, YouTube, and blogs, founders can now level up their exposure to and understanding of fundraising concepts without being inside the strange and obfuscated personal networks of VCs.

Here are a few of my favorites:

But with all this free, amazing fundraising content the problem still hasn’t been solved. Even the most talented founders are struggling to execute fundraises - failing when they shouldn’t, settling for suboptimal outcomes.


The devil’s in the details

The challenge is that all the brilliantly prescribed playbooks, insightful tweets, inspirational LinkedIn videos, in-depth essays, and other published advice can’t cover every situation a founder runs into.

Fundraising is an unscientific system that can change based on market conditions, psychology, and specific situational details.  

For example, a year ago, I wrote and spoke about the power of stacking SAFEs / notes with increasing caps and limited availability as a strategy almost any founder could leverage.

Today, would I encourage most founders to do that? No. Some might be able to but it really depends. 

It depends.

That’s the operative phrase for most things in fundraising. And because of that, as founders find more fundraising content shared on the internet, many times it can feel like the more they know the less they understand!

  • Elizabeth Yin said to do X! But… that doesn’t quite fit this situation
  • Harry Stebbings mentioned Y in his podcast - … why isn’t it working for me?
  • Jason Yeh TOLD me that I HAD to schedule 4-6 meetings a day for calendar density - What happens if I only have 3 on one day???

Advisors to the rescue, right???

But what if you don’t have advisors with the knowledge?  And even if you have advisors with the knowledge, what about when they’re not around?  … or don’t have a great answer??

Parenting your inner child, Advising your inner founder

At some point you will need to advise yourself. I’ve learned a lot about parenting your inner child when it comes to managing my own personal shit.

I’d like you to do the same when it comes to fundraising. Sometimes you’ll have to be your own advisor. 

But how, you ask.

You are probably a deeper expert than you think.  You can be your own advisor.

Your hidden fundraising expertise

I’m a fan of saying that all systems that deal with influencing humans are essentially the same with different vocabulary. This realization can help you build better instincts and confidence when it comes to fundraising. You don’t have to think of yourself as a complete outsider!

Think about a field you DO know well that involves influencing humans.  Here are a few to consider:

  • Software Sales
  • Landing Page design
  • Brand Marketing
  • Social Media Growth 
  • Real Estate

Maybe you never worked in those fields?  What about these?

  • Being on a sports team and influencing your teammates
  • Getting elected to office (student government or otherwise!)
  • Convincing your friends to go on a trip

All of these systems deal with human psychology and can provide you with a reference point or a source of confidence in a pitch.

Ask yourself: 

  • If this were me trying to close a software contract, how would I react?  
  • If this were me trying to convince them to go out on a date with me, what would my response be?
  • If I wanted this landing page for a fundraise to convert well, what information would I include? What type of language?
  • If I had to think about this like a brand marketer, what would I have to consider before publishing this content?

Now of course there are details specific to fundraising that make these situations slightly different. But in combining the fundraising information you’re learning online with your existing expertise in influencing people, you’ll have a great model for advising yourself when you don’t have other advisors around.

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