This is Why Preparing to Fundraise is Hard

Jason Yeh
March 11, 2022

I sent this tweet out like I do most of my tweets – off the cuff and without much thought

If you follow me on social media (Twitter, LinkedIn, etc), you’ve probably noticed I’ve been posting more. It’s the result of a recent effort to help my writing reach more people. 

Sometimes I worry that the casual visitor to my social media channels assumes I’m a wannabe influencer shilling my content like it’s the next trendy energy drink or weight loss supplement. In reality, I work hard to provide the most genuinely useful and actionable fundraising advice for founders. My daily conversations with founders and investors generate the market’s most current and relevant fundraising insights and help us advise founders at scale. 

One principle I teach is the outsized importance of preparation in executing a successful fundraise. The effort that is put in before a fundraise kicks off is where all the magic happens. It's why I launched the podcast Funded. Telling the full story behind fundraises helps disavow founders of the notion that the amazing fundraises they hear about on Twitter were quick or easy. 

Recently, I realized that in pushing fundraising prep, I had skipped the most important part of being a great advisor that I tweeted about.  While I constantly remind people that it’s hard, I have been failing to do the work to truly identify and recognize WHY it's so hard.

Recognizing why

A few weeks ago, the CEO of Flow Club Ricky Yean sent out an email about task prioritization. He referenced what is called the Eisenhower Matrix. The Eisenhower Matrix is a framework to help decide how you execute tasks, made popular by the 34th president of the United States, Dwight Eisenhower. President Eisenhower was president during World War II and as you might expect, had a lot of tough decisions that required prioritization to effectively manage the country in some very trying times. 

The Eisenhower Matrix breaks down all tasks into a 2 x 2 matrix mapped against the dimensions of urgency and importance and helps you decide how to process each combination:

There are the non-urgent and non-important tasks…those are easy. You just delete those tasks. Don't do them. 

Then there's the urgent and not that important tasks. Those things should be delegated to others. 

Another easy one? The urgent AND important tasks…well you should do those right away. 

The last category of tasks, the Important but NOT urgent tasks, is what I think of as the danger zone in the Eisenhower Matrix. These are things that are important to future goals, but lack urgency so are very easy to avoid.  These tasks will get overshadowed by urgent and important tasks that continue to pour in. 

The reason that fundraising prep is so hard is that those efforts land squarely in the Eisenhower Matrix’s danger zone. Like I said, fundraising prep is incredibly important BUT it's also not urgent unless you are running out of capital- in which case you might already be too late to the game.

This is especially challenging for a lot of founders who have a bit of “just in time” cowboy in them. That’s the disorganized founder who runs from task to task flying by the seat of their pants and shooting from the hip. There is some genius to that approach with some founders, but it can be a recipe for disaster when it comes to fundraising. 

So, what do I do about it?

So how do you solve for the tasks that fall into the important but not urgent danger zone category? 

The Eisenhower Matrix would say that scheduling things is the key. Scheduling those tasks so you know you have to do them in a certain time period can help you complete things that don't have built-in urgency or deadlines. 

Here is where I add my own layer of nuance to Dwight’s sage advice.  Scheduling tasks makes sense, but in my experience is easier said than done. I have been encouraged to use this strategy of scheduling tasks that I avoid.  It works sometimes, but it fails more often than not. 

Side comment: I hope you see this is me recognizing why a piece of advice is difficult! So at least I'm learning :) 

So if scheduling is the key, but the key is difficult- then what’s the key to the key? The key is mixing in accountability with scheduling.


But what’s accountability in this case? Here are some tools to help add both scheduling and accountability to your fundraising:

  • Create accountability partners with founder friends who may be doing something similar and on a similar timeline around fundraising. 
  • Schedule regular check-ins with advisors or coaches. You’ll be motivated to provide meaningful updates which requires you to make consistent progress.
  • Give a teammate the specific task of checking in with you on a consistent schedule.
  • Join accelerator programs. A lot of accelerator programs have fundraising preparation timelines baked into their programs. Y Combinator famously drives its companies to prepare for demo day.
  • Schedule a regular Flow Club session focused on fundraising tasks (s/o to Ricky Yean).
  • Explore niche fellowship programs like the one I run, which are much more focused on the very specific task of fundraising prep. 

Learning how to break a deadzone within the Eisenhower Matrix is incredibly important for fundraising and beyond. Incorporate this approach today.

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