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

youtube ↗Offers

When making a guarantee, should it be limited to what we fully control? For example, if we guarantee closed deals but can't control closing, is it risky if clients lie about closing or lead quality? Have you encountered such cases?

Absolutely brilliant question. One of the core things you should do in any guarantee is to guarantee only what you have full control over. If you're booking meetings for people, guarantee the meetings booked, not the closed deals, because once the meeting is booked many things could go wrong based on the prospect's inputs, and you don't want your results to depend on somebody else's actions. Sometimes you're limited to offering guarantees that involve some client input, but in perfect circumstances you should focus on what you entirely control. Outside of our control, a stoic mindset says don't worry, but since it's your business you can construct whatever guarantee you want.

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Related answers

youtube ↗Sales

How do I build trust and guarantee results for a cold lead to make them ready to buy?

You said you almost guarantee results; I guarantee results—I tell you you'll get X, Y, Z or risk mitigation. There's a difference between an emotional sales decision, where people feel they need to buy now, and an intellectual sales decision, which focuses on positive ROI. A guarantee addresses both: intellectually, it removes doubt about returns; emotionally, it feels like a no‑brainer. If you’re willing to guarantee your service—and refund if you don’t—there’s no reason not to move forward unless there’s another unresolved issue, you’re untrustworthy, or you haven’t built enough value. So, just offer a guarantee. Don’t pitch it as a demo; that makes you perform like a dancing monkey. Instead, frame it as one business owner to another: show them something cool you’ve built, like a lead extraction and enrichment system that worked for a seven‑figure business, and let them see it. That puts you on equal footing and feels like sharing something valuable rather than performing for approval.

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youtube ↗Offers

Should I offer guarantees in my offers even if I'm not confident I can deliver them?

Offering guarantees makes you work harder and learn more because your ass is on the line. As Jack Roberts said, show me the incentive and I’ll show you the outcome. If you guarantee a result and must refund if you fail, you’ll push harder than if you just take money without a guarantee. You’re not just promising a result; you’re creating an offer like “I’ll get you 20 book meetings in 60 days or I’ll refund you.” That’s how it works. I was once told never to guarantee anything, which held me back, but now I believe you should 100% guarantee—it’s the minimum entry ticket these days.

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youtube ↗Lead Generation

Would you promise meetings booked for your AI lead generation or outreach system, and how should I position that guarantee given I have a case study for leads? Also, how would I write cold‑email copy when selling business coaching to medium‑sized owners?

You should absolutely guarantee meetings because guarantees align your incentives with the client’s and remove most of the downside. If you screw up you only lose time, but you gain experience and the client still sees value. For example, guarantee 20 sales appointments in 60 days. If you hit the target, the client is happy and you get paid, building a strong relationship for future work. If you deliver between 0 and 20 appointments, the client still gets some results, you may not get paid, but you leave a positive impression because you provided value for free. The worst case—zero appointments—is statistically unlikely; with a uniform distribution across 0‑20 there’s only a small chance of getting nothing. In practice, if you’re competent and consistent, the odds of hitting the guarantee are well over 50 %. That means, on average, you’ll earn roughly half of your fee per client (e.g., a $2,500 fee yields about $1,250 on average). Even when you fall short, you gain learning and goodwill. The key is to set a realistic guarantee, back it with a solid case study, and understand that the guarantee pushes you to deliver and helps you learn faster.

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youtube ↗Offers

What is the basis for qualification and what should I guarantee?

You should create an offer. The offer should look like: I will guarantee you X outcome in Y time, or I'll give you Z. Z could be your money back, a $250 Amazon gift card to your favorite steakhouse, or whatever you want. Basically, it needs to completely eliminate risk for them accepting the offer. Then you look and see if the business you're on a call with can actually achieve what you just said. If they don't have a good sales team and you're guaranteeing revenue, their ability to close that revenue depends on their sales team, meaning they won't be able to help you fulfill your guarantee, so you probably shouldn't work with them. As Hormosi said, virtually all sales calls are just verifying eligibility for the guarantee. When you run offers like this, you're literally on the call to see if your guarantee—say, booking them 20 sales appointments in 60 days or they don't pay—is something this company can actually deliver. You use the guarantee to get them on a call, then verify their eligibility. Some will say, 'Fuck yeah, we can totally do it.' Others won't look capable or competent; in those cases, you don't move forward because you know it's your ass on the line at the end of the day.

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