#278 · upwork vs cold email: which gets your first client faster?

youtube ↗Lead Generation

What do you recommend I do in my free time when running cold email campaigns? I've got all the time in the world, but since email campaigns are automated, I find myself doing nothing a lot. What lead gen methods do you recommend besides Upwork?

Your situation isn't really an issue—you're already using lead‑generation strategies that don't demand daily time. The biggest improvements in life come from doing the same thing consistently over a long period. I recommend a daily lead‑generation activity that requires you to articulate the benefits of your service, such as recording a video or leaving a voice note. Examples include sending DMs on LinkedIn, X, Instagram, or TikTok, or engaging in relevant communities. Talking to people in a social‑media style helps you get 1% better each day at explaining benefits and understanding needs. You can also create personalized icebreakers for large lead lists using tools like Ampify to automate the process.

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Related answers

youtube ↗Cold Email

What is the best strategy for sending cold emails, when did you start your first campaign, how many days did you send them, and after how long did you get your first client?

I started cold emailing around 2018‑2019 with my business partner Gurinder; those early attempts didn’t work well. I kept sending emails for about three to four years before I made any money, and it was probably closer to two years before I saw real revenue. The breakthrough came in roughly 2021 with what I called 'one second copy': I ran many cold email campaigns and offered free sample articles that were produced cheaply using AI, which hardly anyone else was doing at the time. That got me attention from big companies like Kixie. The best cold‑email strategy is to front‑load value—give the recipient more work or benefit than you’re asking for. Instead of asking for free labor, identify a problem they’re suffering from, solve it, and attach the results to your email. For example, I once rewrote 40 YouTube titles for a follower, provided a one‑click doc, and they saw immediate CTR improvements. That’s how successful, ‘rich‑people’ cold emails work: you save them time or make them money, not the other way around.

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youtube ↗Cold Email

How should I get leads with almost no budget? How should I cold DM and email them without social proof? Should I build it as an agentic automation or a simple N8N‑style workflow?

You can generate leads on almost no budget using the Appify scraper—it’s about as cheap as it gets. If you try to go cheaper, you’ll trade off a lot of time. You could even resort to low‑tech methods like handing out flyers, but that’s far less efficient. The realistic approach is to manually compile lists on X, Instagram, Reddit, etc., then cold‑DM or email them. Ideally you’d have some social proof, but if you don’t, you can create it by showcasing marketing results: prove you can consistently book, say, ten meetings a week. Once you’ve demonstrated that, you can sell the service itself—offer to install the lead‑generation system in a client’s business and manage it for free until you hit a target, or guarantee a set number of meetings per week and only get paid if you deliver. This way you monetize your ability to book meetings rather than a product. The workflow can stay manual; you don’t need a complex automation at this stage.

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youtube ↗Lead Generation

How should I start and run a speed-to-lead business: test 100 businesses with landing pages, measure lead response time, then pitch via cold emails—should I personalize based on gaps or send mass cold emails?

You can assume almost all businesses have speed-to-lead problems, so you don’t need to research each one. Instead, scrape leads and assume they have the problem; this works about 80% of the time and is much easier. By framing the issue as their specific problem, you can send cheap, high‑volume cold emails and still close deals.

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youtube ↗Cold Email

I want to start a cold‑email outreach but only have manual tools—what should I do?

I’ve been in the same spot. I started by rotating a handful of Gmail accounts—sometimes five—sending about ten cold emails a day from each. It’s not ideal, but it works to get started as long as your emails are well‑researched and the approach is solid. Gmail accounts have lower deliverability, especially new ones, so they need to warm up. You can also buy cheap inboxes (e.g., three Instantly airmail inboxes for around $4 each per month plus a domain) which gives you roughly 90 emails a day. Build a quick lead list, template your messages, and spend the first hour‑and‑a‑half each day sending them. You can also DM prospects. The key is to keep sending, refine your copy, and don’t worry too much about the tools at the start.

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