This week, I launched my first SaaS ( and crossed 100 conversations with prospective Chatty customers. 5 of those put credit cards down to take the free trial. But this isn’t the idea I made money from this week.

I’ve been doing Free Sales Advice Friday for months in communities like Visualize Value. Being a professional salesperson, it’s pretty straightforward. Someone drops the name of their business, I take 10 minutes to write a scrappy plan for how I’d sell their product. They find it very helpful:

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It’s roughly the same every time. Someone has an idea, builds it, but doesn’t know how to find customers. I share how I’d find their people and what I’d say to them. At the same time, so many people have been asking me how I hustled to get beta users for Chatty. I started to ask if I should build something to help bootstrappers win at sales. The response:

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So I wrote a report: 1 Tip, 1 Tool, and 1 Teardown. I sent it out to the people I’ve been doing Free Sales Advice Friday for. I told them I was testing the waters on a premium newsletter to help Bootstrappers win at Sales. This was focused on generating sales from your first 100 targets. The response:

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2 presale subscriptions in the first day. More money than I’ve made from Chatty so far. Profitable before I even started.

I’ve talked to 31 people so far, and I’m going to talk to 100. I’m giving myself until next Monday to presell 10 spots to get this idea of the ground. I definitely feel like I’m hitting a zeitgeist here: People are tired of the 12 startups in 12 months concept. It leads to un-used, un-validated ideas. Lost time and products nobody wants. And the worst thing of all: otherwise well-meaning boostrappers losing money and confidence in themselves.

So I’d like to introduce a concept. The Rule of 100. 1 idea, as long as it takes you to speak to 100 prospects. If you can pre-sell at least 10 people on your concept, build the damn thing. Do this before you go building things. Let’s build from a place of strength, with users who have skin in the game.

I’m eating my own dogfood here by preselling this newsletter, where I’ll also be expanding on this process. I also realize this invalidates Chatty (at most, 5 paid users from 100 conversations). And I’m ok with that. I’ll let it run in the background for a while to see if anything else happens, but I’d rather work on the idea people are offering me money for.

I’m filling a few more spots for my newsletter on sales for bootstrappers. If you’re interested in helping me get it off the ground, email me at

Tagged #Personal, #Projects.