When most first-time founders think of fundraising, they think this.

They envision building a sexy deck, pitching with tons of emotion, and negotiating with sharks…

That isn’t fundraising though. The reality of fundraising is that it mostly is one very boring, extremely unsexy thing over and over and over again.  

Welcome to Project Management Hell ❤️‍🔥

When you actually get into fundraising, you’ll find that the majority of the hard work is repeatedly getting people to do what they said they would do.  

Here are some examples:

• Asking teammates for numbers to include in materials
• Emailing VCs to schedule meetings
• Following up with lead investors to deliver term sheets
• Nudging non-lead investors to send round commitments
• Corralling all committed investors to wire checks

And maybe the most difficult project management challenge… ensuring YOU actually do the work you know you need to do.  The last one is non-trivial…

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How to escape hell (or at least manage the heat)

Unfortunately there’s no escaping this hell. Project management hell is a required stop along the way to Venture Capital City. You can’t avoid it, but you can make it more manageable by giving it some well-thought-out structure.  So at least you won’t be PM’ing like a chicken with its head cut off (that is truly a fiery inferno).

Here’s how you get to a more Miami-in-the-summer style hell…

First, start with an outline

List everything that you’ll have to do to execute a fundraise. Don’t do what some founders do and learn on the fly. They THINK they know how to start and then assume they can ask questions along the way.  This is a recipe for disaster… and why do that when you have such great resources to help?  

Here’s a Gantt chart of how I think fundraises play out:

And why not ask our dear friend ChatGPT what they think. The answer I got wasn’t perfect but it’s a great start!

Next, PLAN.  For the love of god… plan.

Now that you see all the work that is necessary, you’re going to have to do a ton of planning.  

Have you ever heard of the Eisenhower Matrix? I’m obsessed with it.  The Eisenhower Matrix is a breakdown of task prioritization mapped to a 2x2 matrix of Urgency and Importance.  There is a danger zone in the Eisenhower Matrix which is the upper right hand quadrant of High Importance and Low Urgency:

And wouldn’t you know it… the vast majority of fundraising prepwork falls into that danger zone.  In other words, most of fundraising prep is EXTREMELY important to do, but doesn’t feel urgent until it’s too late.  

The common guidance for navigating danger zone tasks in the Eisenhower Matrix is to schedule the work.  AKA… project manage.

When it comes to planning, it's important to break down the fundraising process into smaller, manageable tasks. For example, you might think your tasks are to research potential investors, create a pitch deck, and schedule meetings with investors. The reality is that each of those things could be broken down WAY smaller.  Creating an outline of a deck is a better initial task. Asking your co-founder and advisors for feedback on the outline is another more manageable task.

By breaking down the process into smaller steps, you can more easily manage the project and ensure that each step is completed on time.

Communicate the Plan

Communication is key. When project managing your fundraise, effective communication with all stakeholders at a micro and macro level will set you up for success.

Great macro communication means informing your business partners, your team, your advisors, and your family about what to expect while you're fundraising.  This will help them understand the changes in your availability and daily schedule as well as the source of your increased stress levels.  A good example of this is providing regular updates on the fundraising process (use mail merge to save time) and answering questions for your teammates, investors, and other advisors. By keeping everyone in the loop, you can ensure that everyone is on the same page and working towards the same goal.

Strategic communication at a micro level means setting expectations that make it easier for you to project manage the process.  For example, when asking for an introduction, explain to connectors why it's important. Something as small as “I’ve just launched my process and it’s important that all my intros get made this week” will help emphasize their need to prioritize your ask.  In addition, simply telling someone you’ll follow up if you don’t hear back can transform your ability to project manage the tasks. By setting the expectation that you’ll follow up, you eliminate the hesitation or guilt you normally feel when bugging someone to follow through on a favor.

Add accountability to project manage YOURSELF

Project-managing the vast fundraising research/execution you need to do necessitates a difficult balance. Unfortunately as the Founder, you have to be the chief fundraiser but that’s the second full-time job you have on top of being CEO and running the company. That means it will be extremely tempting to avoid some of the more painful and mind-numbing fundraising work in favor of doing things for your company.

One trick to help keep you on task is to find an accountability partner or group. While the Founder/CEO has to be the main person responsible for fundraising, a co-founder, employee, advisor, coach, or friend can help keep things on track as an accountability partner.

Weekly check-ins where the CEO shares a fundraising update are simple but extremely effective. My check-in meetings generally look like this:

1. What activities did I accomplish the previous week
2. What do I plan on accomplishing this coming week
3. What is the status of the various processes that are in flight

Technology and Systems!

Check-ins only work if you’re tracking your process.  It’s garbage in garbage out if you show up to these meetings trying to reference your email inbox or your memory.

I highly recommend you implement a CRM system and/or project management software to help keep yourself organized.  You want to know who you’re talking to, how you got to them, what the status of your engagement is, what next steps are… and you want to be able to look that up instantaneously.

My spreadsheet-based CRM is a good starting point -> download here

But if you’re comfortable with more advanced CRM systems, you have a few options.

• Sales CRMs - systems designed for sales teams like Streak, Pipedrive or even Hubspot can be retrofitted for the fundraising use case.  
• Fundraising CRM - Foundersuite is a well regarded CRM purpose built for fundraising. Sign up here and use the code “JayYeh” for 30% off the first month of a Monthly plan for 30% off a full year of the Annual plan.
• Homegrown - you can use Airtable, Notion, or any other relational database to build a more dynamic system that can be customized to your exact liking. This option takes a little more effort, but if you’re comfortable with those tools you could get to a great solution (this is my favorite)  

Turns out, you’re just a project manager 😛

When you started down this path, you might have envisioned a lot of high-profile work that would land you interviews with TechCrunch, conference invites, and magazine covers…

This could be you!

Ultimately, the life of a CEO is not that glamorous. Your job is to do whatever needs to be done. Sometimes that means being the janitor, and on the fundraising trail… that means being a project manager.

It might not sound sexy, but by planning, communicating, and holding everyone accountable, founders can stay on top of the many moving pieces required to successfully raise capital.