Quick context: My friend is the founder of an ed-tech company that aims to revolutionize learning experiences. She had to get creative to close her seed round in just 17 days, starting with zero investor contacts.

Everyone kept telling her to "schedule all your investor meetings in a 2-3 week window to create FOMO" like in that classic YC post. Great advice if you already have a network. She didn't.

So she got a bit desperate and tried something unconventional that ended up working: reverse-engineering her competitors' cap tables to build her target list. Here's what she did:

First, she started by identifying her real competitors. Not just the obvious ones, but companies solving similar technical problems—even in completely different markets. She ended up with about 25 companies using Crunchbase Pro (worth the $) and manual digging with Tracxn.

Next, using a combination of automation tools, spreadsheets, and data sources, she connected to Crunchbase, investor websites, and her own research data to analyze the ENTIRE portfolios of investors who backed her competitors. This helped her spot interesting patterns—like investors who never explicitly mention her space but have backed 3-4 companies using similar technology stacks.

She discovered investors she wouldn't have considered otherwise. One of her term sheets even came from a firm that primarily backs healthcare startups, but had a hidden pattern of investing in her company's underlying technology.

For outreach, she ditched generic templates. She used Apollo.io to find emails, then leveraged various general-purpose automation and personalization tools to generate highly customized messages by synthesizing data from her CRM, investor social profiles, and their portfolio information. Each message referenced specific companies in their portfolio and articulated exactly how she connected to their investment thesis. Time-consuming, but the response rate was amazing.

She sent emails in three waves to create a natural meeting cadence: Monday: Top 15 dream investors Thursday: 25 strong matches Following Monday: 30 more prospects

She used Calendly to avoid the scheduling nightmare. Having separate links for each wave kept things organized when responses started flooding in.

Final stats: 70 cold emails 42 responses (way better than she expected) 31 first meetings 5 term sheets Closed $2.7M at $15M valuation

The biggest surprise was how well the personalized outreach worked. She used Streak to track opens and automate follow-ups, which helped catch several investors who initially missed her email.

For YC companies specifically - don't save your metrics for the meeting. Put your best growth chart right in that first email. She found that significantly bumped her response rate.

The fundraising experience convinced her of the power of leveraging modern tools and automation to streamline outreach and due diligence. She's since helped other founders use the same playbook to raise more efficiently (and honestly, you could stitch together most of this with the set of general tools and tips mentioned above if you're on a budget).

She is happy to answer questions or share more details if helpful. Still kind of shocked this actually worked. The overall approach proved highly effective for raising a seed round for her ed-tech company.