๐ How I Would Raise Capital Today with AI (If I Were Starting From Scratch) Fundraising in 2025? It's not about grinding harder. It's about stacking leverage. AI gives you the unfair advantage most founders still aren't using—but here's the real unlock: If you don't have warm intros, your #1 job is to get them. Yes, you should still run cold outreach with AI (and I'll show you how), but the entire goal of the system is to turn cold into warm—and warm into wired. Because here's the truth: Cold email gets ignored. A warm intro from a founder the investor already trusts? That gets opened. Every. Time. And before we dive in—run this like a real process. Drive people toward key dates. Create an actual investor pipeline. Move them through each stage together. This will make you seem less desperate and condense your process to 3-6 months rather than 12 (or worse). 1. Build a Prospect List in a Day (Not Months) Instead of manually hunting LinkedIn profiles and stalking TechCrunch articles, I'd prompt ChatGPT to generate an investor list in seconds. ๐ Prompt: "Find 250 active early-stage investors who have backed companies similar to [insert your startup's niche]. Prioritize those who have made investments in the last 6 months." This is the foundation for your warm intro map. Once you've got your list, don't just stop at investors—look up their portfolio companies. Now use AI to: - Identify the founders of every PortCo they've invested in
- Build a database of those founders
- Follow them on LinkedIn and Twitter
- Engage with their content, ask thoughtful questions, share insights
- Reach out with value-first DMs or emails
- Set up coffee chats, Zooms, or real-world meetings
Why? Because founders get hit up far less than investors do, and they're much more open to connecting if you're genuinely useful. Be clear about how you can help—then, after building real rapport, ask for intros to their favorite investors. This one month of upfront effort is worth a million cold emails. 2. Qualify Investors like a Top Sales Pro Not every "VC" is worth your time. In fact, most are not. Filter hard. I'd run the 250 names you generated through an LLM (like GPT-4 or Perplexity) trained on public deal history, Twitter, Medium posts, etc. ๐ Prompt: "Summarize the last 10 investments made by each investor. Rate alignment with [my company] on a scale of 1-10." Overlay that with intel on which investors are active, aligned, and accessible. And yes—use social listening to see who's actually engaged in deals vs. just vibing on Twitter. By this time you should have trained ChatGPT on exactly what your company does and where it's going. Now instead of cold emailing everyone, I'd target the top 20%. 3. Create Personalized Pitches at Scale Forget spraying the same bland "We're raising a seed round" email to everyone. Use an AI email generator that pulls insights on the investor's interests and their last deal and ties it to why your company matters to them. ๐ Prompt: "Write a punchy 75-word email to [Investor Name], referencing their recent investment in [Company] and positioning [My Company] as a complementary play." Remember, your subject line matters most. When in doubt just use the investors first name as the subject line (i.e. "Sean"). ✅ Bonus: Create a style guide to train the AI to speak in your exact tone and voice. I've done this with POE to ensure people don't receive generic comms. ๐ Double Bonus: Create a HeyGen avatar that allows you to send custom video messages to hundreds of investors without having to do any filming yourself. I just created mine and have no doubt video avatars are the future of communication. ⭐️ Triple Bonus: SEND OUT handwritten cards or some package in the mail. In the age of AI, nothing takes the place of tactile, real-world touch. I'm blown away that more founders do not do this. It's the TOP conversion tactic I would use. 4. Follow Up Like a Machine The worst part of any sales process is almost always the follow-up slip. Whether you're a founder selling your company to investors or a sales professional selling your service to a potential client, follow-up is the first thing to fall through the cracks. Which sucks, because it's often where the money is made. The solve? Set up automated, personalized drip sequences using an AI sales system: - 1st follow-up: 3 days after no reply
- 2nd follow-up: share traction update or quick win
- 3rd follow-up: inject scarcity ("Have 300k left in round, closing EOM")
- Go-forward: Long-term nurture (even if this means reminding you to send a personal ping and note—investors like to invest in lines, not dots, meaning start building relationships with multiple touch points today)
5. Move Fast. Kill Slow No's. If they're not leaning in within 14 days, move them to a low-energy nurture list. Don't get stuck trying to "convince" anyone. Find the believers. Anything else is a waste of time. Meanwhile, engage publicly: - Comment on investor posts
- Join their AMAs
- Add value in their circles
- Tag them in wins (sparingly)
AI can help you speed-run to them—if you let it. Bottom Line? AI helps you automate the cold. You bring the human touch that makes it warm. Warm intros close rounds. Bold founders close fast. And the best ones? They do both—with AI as their copilot. |
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