#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.

cold emailventure backedpress releasescrunchbase
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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.

cold emailhyper-customizemulti-platform
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How can I personalize cold emails for clients who lack online presence, like handyworkers, so the outreach doesn’t feel like an ad?

Treat the prospect as a fellow tradesperson—mention your own background in the same trade (e.g., ‘I’m a plumber’ or ‘I’m an underwater welder’) to create shared experience and familiarity. This light personalization works better than a generic cold email and serves as a solid fallback when you lack specific details. You can also use a ‘cold read’ approach, disclosing intimate familiarity or referencing a shared group, which boosts influence and reply rates.

cold emailpersonalizationhandyworkersicebreaker
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Can you do a step‑by‑step for somebody looking to do their first cold email campaign at a small scale? How would you structure a campaign on Instantly?

I already recorded a video that does all this called "Watch Me Start and Sell an AI Service in 10 Hours" where I go through the process of finding a need, picking niches, finding needs via Reddit, converting them into offers, putting offers into Instantly, scraping and uploading lead lists, reaching out, and I usually get about 10 interested people who want to book calls within an hour and a half of work.

cold emaillead genstep-by-step