#161 · Here are the 7 pain points I press on every sales call (demo)

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What tips do you have for using cold email and voice outreach to attract investors for a startup, especially when you earn a commission on the investments you bring in?

The creator outlines a straightforward investor outreach process: first build a list of target investors in the relevant niche (e.g., ad tech). For each investor, use a tool like Perplexity or an OpenAI web search to find their last 10 investments and a brief summary of who they are. Use that information to personalize a cold email—reference a recent investment, explain why it was strategic, note that you’re now working with a company that fits their thesis, and offer to share a pitch deck or more details. He also suggests pulling the investor list into LinkedIn to find mutual connections and request intros, but notes that this takes longer. Because investors see many deals daily, he prefers a one‑shot approach: send the personalized email, collect the positive responses, remove those leads, and then optionally follow up with a more nuanced connection request on the remaining prospects.

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Related answers

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How should I set up cold email to reach venture‑backed startups?

You can build a venture‑backed startup list in two ways. First, monitor press releases and announcements—many have RSS feeds. Use AI to filter for new funding announcements, extract the company name, then look up the LinkedIn URL and website to find employee emails or add them to a LinkedIn outreach sequence. Second, use a paid database like Crunchbase: for about $199 a month you can scrape up to 5,000 rows of funded companies, which gives you a ready‑made list of prospects with websites and LinkedIn profiles to pull contact data from.

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With zero budget and no proof, what outreach strategy and daily actions would you recommend to land the first client for an AI receptionist agency using cold emails?

You already have the product, offer, and demo, but you could have validated the market first—sell the idea before building the product. With no budget or proof, focus on hyper‑customized cold outreach: research each prospect deeply (e.g., find an old blog post) and mention it in a personal note. Instead of blasting 100 generic emails a day, send about 20 highly tailored ones and follow up on every platform where they’re active (Instagram, LinkedIn, X, TikTok). This multiplies your visibility—reaching people on three or four platforms can give you two‑to‑three times more exposure than email alone. Assuming a 20% chance of being seen per platform, outreach on several platforms raises your overall view rate to about 50%, which can yield a 25% reply rate. From 600 outreach attempts you might get ~75 replies, ~10 positive, leading to a few calls and possibly one closed deal.

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I’ve built an automated personalized outreach system but have almost no credibility. How should I market my system?

Even with zero credibility you can still get traction by using a conversational tone in your outreach. Write longer, personalized emails that give context about who you are, what you’re building, and why you’re reaching out. Make it sound like a genuine conversation rather than a sales pitch. This approach works well for beginners because it feels authentic and helps you stand out from the generic offers flooding inboxes. Give it a try – the personal, story‑driven style often lands the first leads when you don’t have a brand reputation yet.

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How can I deeply research prospects and personalize cold emails when I find it hard to get information? How deep should research go, and can you give a quick guide?

Don't personalize the whole email—personalize only small snippets using enhanced variables. For example, use a template like 'Hey {first name}, love {thing we have in common}, fun to see you mention that on {platform} where I got it.' Then continue that vein to your offer. If AI writes the whole email, it will likely produce something stupid and obvious as AI‑generated. Keep the AI constrained everywhere and feed it only small variables (enhanced variables) with examples, letting it spin the initial info into a tightly woven, human‑sounding message. For research, use Claude to look up the person, compile company info, and grab all social media profiles; if you can't, use scrapers or similar tools.

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