I guaranteed a client 20 meetings in 60 days and now worry about cash flow; what should I do?
When you make a guarantee like 20 meetings in 60 days, you need to get payment up front. Instead of working for free until you hit the target, have the client sign a contract and pay you before you start. If you miss the goal, you refund them. This upfront payment solves cash‑flow issues, shows both parties are serious, and gives you billing details that make upsells easier later. Even though asking for money upfront can be harder, it protects you and builds trust.
There are basically two approaches to billing a first client. First, you can offer a guarantee—guarantee service or performance. If you don’t hit the guarantee, you give them all their money back. When you do any kind of guarantee, take all the money up front; you need everything you need up front because if it doesn’t work you’ll just refund it afterwards. Second, if you don’t have a guarantee (some industries or deals don’t make sense for one, or you can close a deal without it), do a 50/50 deposit on a fixed price: stake 50 % up front and the remaining 50 % upon delivery. This gives the client some risk mitigation while still being technically performance‑based, since the performance is the delivery of the project. People are a lot more likely to say yes to a custom scope if they’re not paying all the money up front. You can also milestone or tranche the payments—three, four, five, ten milestones, etc. I’ve seen some pretty crazy ones, especially in enterprise projects where multiple tranches are sometimes needed, but I don’t usually recommend that approach.
Don’t work without upfront payment unless you have a clear guarantee. For a late payment, follow up politely every few days, consider a partial‑payment arrangement (half now is better than zero), and in future always collect at least a token commitment to avoid chasing.
No, I don’t offer deferred or success‑based payment. I require an upfront fee because commitment needs skin in the game; it’s viewed as a deposit that’s refunded if you don’t get your first client in 90 days. Without some upfront investment, accountability drops and success rates would plummet.
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.