The 20% rule

It is called "Email It: A Seller's Guide to Emails That Work" by Bill Caskey and Bryan Neale. I was expecting some email templates. 

What I got was philosophy.

The first two pages laid out four principles for selling. One of them was abundance. The idea is simple: if you're nervous about whether a deal will close, you're not talking to enough people. 

Because if your pipeline is full, no single prospect has power over you. Your behaviour changes. You listen better. You stop chasing. People sense it, and they trust you more. The timing and flow of the deal are more natural. 

I used to mentor business owners who didn't know how to sell. They'd come to me stressed about a deal, and I'd tell them the same thing every time: the answer isn't what do I do next on this sale. 

Neither is obsessing over saying the right things in the right order (and thinking it will change the result). Your professionalism and expertise do matter, but often the sale has its own trajectory and rhythm. 

Instead, as previously outlined: you're not talking to enough people. Talk to more people, and this problem disappears.

That PDF is stuffed in a slightly more ordered folder than my downloads: it’s named “strategic documents”. It sits proudly with my collection of largely quadrant-based models (looking at you, Ansoff’s product market matrix). I pull it out periodically, and it’s like I’m hearing the lessons for the first time. 

I went looking for it this week because of a conversation I had with Dante St James on Slideshow with Dave Hayward in our latest episode.

Dante is a serial entrepreneur based in Darwin. He runs six cafes, three menswear stores, three barbershops, and three training businesses. He's also a LinkedIn Top Voice and a contractor for Meta, with seemingly endless depth, expertise, and intellect. 

His first cafe cost him three COVID-era plane tickets, which admittedly were not cheap ($18k). 

In April 2020, a Brazilian family in Cairns was trying to sell their cafe so they could get home to family as the pandemic closed borders. No one was buying cafes as the world shut down. They posted in a Facebook community group, growing more desperate each week. Dante reached out, heard their story, and asked what it would take. Their answer: pay for our flights and the cafe is yours. Staff included.

Two weeks later, Australia locked down. But Dante's team found a portable coffee cart, got permission to set up inside a local government building where workers couldn't leave to get coffee, and started serving. 

Then the state government offices wanted one. 

Then he needed five carts. 

Asset finance companies thought he was mad until he showed them the memoranda of understanding from government. $125,000 in coffee cart financing later, and the cafes funded everything that came after.

Dante’s 20% rule is a spiritual sibling to Caskey and Neale’s abundance philosophy. But it’s about a lot more than selling.

No single activity he does can account for more than 20% of his total income.

He thinks of his businesses as fire hoses. If one dips, he turns up another. If one fails completely, he loses 20%, not everything. And he can replace that 20% by finding more work in an area that's already running.

He's not casual about this. He has 72 people on payroll. Their mortgages and rent depend on him. But the structure means no single failure is fatal. And that changes how he operates: he starts a new business almost every month, expects most of them to fail within two or three weeks, and moves on without ego.

I asked him about stress. His answer: "I've gone through enough failures to know that you don't die."

Most of the businesses I work with have the opposite problem. They get busy, love the work, do the work, and come out the other side with no pipeline. 

Then the couple of months with no revenue eat all the profit they made during the busy period. Feast and famine. This is rife in professional services and tech. 

It happens because marketing and business development feel like something you do when you need work, not something that runs as a system. Dante calls it the difference between marketing as a tactic and marketing as a strategy. 

The tactic is: I need a thing, so I go and get it, and then I stop. The strategy is: what am I doing to make sure the next thing is always on the way?

Dante made a sharper point about employment, too. He believes the most dangerous position in 2026 is having a single source of income. A full-time job is maximum concentration risk. Whether you agree with that or not, the principle scales to businesses: if one client, one product, or one channel accounts for most of your revenue, you're one bad quarter away from trouble. 

And when I say “you’re”, I was, of course, mentally turning over my own financial situation in my head. I’m 100% all in on Europa, but Europa is made up of several customers. Our marketing is definitely always on; the pipeline is pretty good. But is it enough? And does having one business with several customers count? I’ll have to ask Dante next time I have him on the show. 

The full conversation with Dante St James covers a lot more ground: medicine to bartending, buying cafes in a pandemic, building a content engine on LinkedIn, and why failure is his greatest superpower. It's one of the best conversations I've had on the show.

Cheers, Dave