After sending an initial cold email proposal, how should I maintain momentum with the client—should I keep sending new proposals for each follow‑up, or establish a streamlined process for ongoing collaboration and upselling?

#114 · $350K/M AI Automation Expert Answers Questions For 80Mins

After sending an initial cold email proposal, how should I maintain momentum with the client—should I keep sending new proposals for each follow‑up, or establish a streamlined process for ongoing collaboration and upselling?

You should aim for a retainer or monthly subscription instead of sending a new proposal every time. Bundle your deliverables into a recurring package—e.g., X systems per month, a weekly strategy call, daily Slack availability, etc. You can also charge hourly, but a retainer minimizes friction on follow‑up projects and keeps the relationship smooth. Include any legal terms like IP, NDA, or unsolicitation clauses in the agreement.

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Related answers

youtube ↗Sales

How should I follow up after sending a proposal and Loom video?

Follow‑up cadence matters. I recommend reaching out every 48 hours rather than daily or hourly, giving prospects breathing room. After sending a Loom video, you still need to send a written proposal they can sign. The proposal creates a transformation event, but remember that signing doesn’t guarantee payment—clients can still disappear. Define a clear transformation and use it as a trigger for automation, such as sending a follow‑up if payment isn’t received within X days. When crafting follow‑up emails, keep them concise and value‑focused. Example scripts: “Hey Pete, just checking in on the proposal. Let me know if you have any questions. Thanks, Nick.” or “Hey Pete, I noticed you haven’t opened the proposal yet. I wanted to bring it to the top of your inbox.” Add value by sharing industry news or free resources, but avoid changing the scope of work. Consistency and adding value are the 80/20 of successful follow‑ups.

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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 ↗Client Acquisition

Should I focus on cold email or Upwork to reach $5‑10 k per month, and if cold email, what tips would you give to start?

You have three main approaches: cold email, Upwork, or both—and you can also upsell existing clients on follow‑up work. There’s no need to pick just one; you can do both and see which works better. If a client is already getting great value from your automation, pitch them on additional scope or an incentive‑based arrangement. To start with cold email, consider the offer size, niche, and daily email volume per mailbox, and test different tactics to see what yields results.

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youtube ↗Cold Email

Is there a free way to automate cold email follow-ups, and can I send more than 10 emails per day safely if I buy a domain and dedicated email?

Nick says spending an hour on follow‑ups is normal and part of the game; in his door‑to‑door marketing days, most outreach time was spent on follow‑ups, and they later moved to cold calling and phone sales, with the first two hours of the day spent following up on warm leads. He explains that money is in the follow‑up because even slight interest is hard to get from a cold offer, so you want to squeeze that interest as much as possible. Regarding automating follow‑ups: if they’re templated, you could automate, but he prefers personalizing follow‑ups when possible, especially if the prospect showed personalized interest. He notes that free automation tools exist (like connecting via make.com or using Claude routines) but at scale you’ll need to do more, implying paid solutions are necessary.

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