Are You Ready to Raise VC?

In the past two weeks, I've spoken to 8 different founders who responded to my LinkedIn post about fundraising. When I asked what they'd done to prepare, the MOST I got was that they'd created a pitch deck and built a target list of ~50 investors.

That's it.

I've been writing about funding and startup culture for almost two years. I've never been more confident about this: the reason for the funding inequities we see for different demographic groups and for first-time founders is that people don't know how to raise money. It's not that they can't or that they aren't building VC-backed businesses. It's just that they're doing it wrong (and that the system isn’t equitable, but, yeah).

So please, please, if you are raising, do it right. Prepare accordingly.

To help you out, I've extracted a bunch of content from my CREAM e-book to create a fundraising checklist. Beyond the list itself, I'll share one key insight for each section that has helped me and the founders I've worked with navigate the fundraising process more effectively.

Let's dive in.

The Ultimate Fundraising Checklist

When you're raising venture capital, preparation is essential. The more prepared you are before you start having conversations with investors, the more efficiently you can run your process and the higher your chances of success.

Below is a comprehensive fundraising checklist I've put together based on my own fundraising experience and what I've learned helping other founders. I've organized it into five key areas:

1. Financials - Your financial model, market calculations, and other numerical validation

2. Pitch Materials - The assets you'll use to communicate your vision and traction

3. Data Room Setup - How to organize and share your company information

4. Communications - Templates to streamline your investor interactions

5. Investor Pipeline - How to build and manage your relationships with potential investors

Every item on this list helped me close our pre-seed round and has supported countless other founders I've advised.

Key Takeaways

Market Sizing

Most founders default to saying, "Our total addressable market (TAM) is $5B, and if we just capture 1% of the market, we'll be a $50M company.” This approach doesn't impress investors.

Instead, use a bottom-up approach. Calculate your SAM by multiplying the number of potential customers by your average sale price.

For Chezie, it breaks down as:

• 57k companies with ERGs

• $45k average contract value

• 57000 x 45000 = $2.63B

$2.63B is our addressable market. From there, we assumed a 20% market share, based on comparable HR tech companies like Workday, resulting in a $513 million obtainable market.

This level of specificity demonstrates you've done your homework and signals to investors you're a serious founder who understands your market.

Pitch Deck

Create two versions of your deck: one for sending and one for live pitching.

Your presentation deck should be minimal—use big fonts and graphics with no more than 10 words per slide. You want investors focused on you, not reading dense text.

Your shared deck needs more detail since you won't be there to explain it. Include complete sentences that describe your solution, clear context for metrics, and enough information that someone can understand your business without you presenting it.

This dual approach ensures that you maintain control of the narrative in meetings while providing sufficient detail for investors who review your materials later.

Here are some side by side comparisons of specific slides from our pre-seed bridge:

Data Room

Your data room should also have two versions, one for each stage of the process.

The primary data room contains just your pitch deck, financial model, and market calculations—documents you're comfortable sharing after a first meeting.

The secondary data room, which your lawyers should help create, includes sensitive materials like incorporation documents, team backgrounds, cap tables, and financial statements. Only share this with investors in full due diligence who have expressed genuine interest. Using a platform like DocSend (not sponsored - it just works really well) allows you to create individual spaces for each investor and track who is viewing your materials.

Communications

After every investor meeting, you’ll need to send a follow-up. Create a reusable template that you can personalize with meeting-specific details.

The template should thank the investor for their time, reference something from your conversation, and provide links to your data room. It should be no more than five sentences long.

This approach saves time while ensuring you maintain momentum in your fundraising process. Having this ready in advance means you'll never miss a follow-up, which is crucial when you're taking multiple meetings per day.

Investor Pipeline

It sucks, but VC runs on warm intros. I’ve written about this before, and every time I do, I remind my audience that it will probably never change (at least not before anyone reading this needs to raise).

That said, always push for warm introductions, even when it requires extra effort.

Cold outreach should be your absolute last resort. VC runs on relationships, and many investors won't meet founders without an introduction. Don't be shy about leveraging second-degree connections—if you're connected to someone who knows your target investor, ask for an introduction to that person first. It might take longer and require more steps, but the difference in response rate makes it worthwhile. Map out these connection paths in your investor CRM to keep track of who can introduce you to whom.

The Bottom Line

Fundraising can be as arduous as you make it. As a first-time founder, you're going to make mistakes, but don't make the mistake of not being prepared.

I created this checklist because I wish I'd had it when I started raising. It would have saved me countless hours, prevented numerous awkward investor conversations, and likely helped me close our round faster.

Remember that investors aren't just evaluating your idea or your traction; they're evaluating you. Your level of preparation signals your professionalism, attention to detail, and understanding of the fundraising process.

If you found this helpful, please share it with other founders in your network. If you have questions about any part of the fundraising process, reply to this email!

Catch you next week,

Toby