#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 makes a lead generation cold email system valuable and how does it compare to traditional outreach?

The most valuable part of a lead‑gen system is its scale. In the past I had to door‑knock, walk to each business, deliver a pitch, and wait for a decision—maybe one or two minutes per prospect plus travel time, so I could only reach 50‑80 businesses a day. With cold email you can send thousands of messages in the same amount of time it takes to write one campaign, instantly multiplying your leverage. Once the email is written you can reach a million people, giving a much steeper rise‑over‑run curve than cold calling or manual outreach. After the initial setup, the results far surpass the effort of doing it yourself, especially when combined with AI personalization that makes each email feel one‑on‑one.

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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

Should I focus on getting clients first and learn skills later, or build skills and automations before acquiring clients? What to do while warming up cold emails?

To be fair, we cover all this in Maker School, but I'll still dangle the carrot. There are other lead generation mechanisms you can use while warming up emails. Upwork is big—apply the same approach I recommend there: record customized Loom videos and send them via cold DMs instead. Find creators, influencers, or people doing work you think you can help with, record a video solving their problem, and send it across their social media platforms. There's a lot you can do here, but I wouldn't just wait 2 to 4 weeks; you could send many customized DMs in that time, and many would likely respond.

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