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The Best Salespeople in the World Make It Rain Money - Here’s How They Do It

by | Apr 3, 2023 | Startups

All great careers, to some degree, become sales jobs.

Sam Altman (OpenAI / CHatGPT)

I’ve been in sales my whole life. Except I didn’t know it.

Then at around 19 years old a farmer sat me down and explained to me how life works.

“You sell a university on why they should accept you. You sell a boss on why they should hire you. You sell a date on why they should sleep with you. You sell your romantic partner on why they should have kids with you.”

I couldn’t sell to save my life.

A farmer showed me how. Here are the principles that helped me make it rain money in my sales career in banking/tech.

The hardest part about sales isn’t the prospect

Selling to someone can be intimidating.

The challenge isn’t them, though. The obstacle in your way is your excuses about why the person will or won’t buy.

Sales guru Alex Hormozi says, “A sale always happens. Either you sell the other person on your solution or they sell you on their excuse.”

When you let the prospect’s excuse fly it’s a form of giving up.

But when you believe they must have what you’re selling, there’s a high chance they’ll change their mind. When you believe, they believe.

The Tim Ferriss strategy that gave him the career he has today

Many people know Tim Ferris as a famous author and podcaster.

What they don’t know is his background in tech sales that set him up for life. Right outta college he got a gig TrueSAN Networks selling storage hardware.

Like the deadbeats they were, Tim and his colleague Bryan had a desk right next to the fire exit in a 4-feet wide space (think of the movie Office Space).

They had the worst job: sales. They got paid $40,000 a year and often had to sleep under their desks. Cleaning crap off Jeff Bezos’s shoe for $2 an hour would have been a better job.

Tim had to cold call CEOs and CTOs. He tried at all different times to reach them. By accident he found that 7–8am and 6–7pm were the best times to reach decision-makers because gatekeepers weren’t around then.

Another tactic Tim fumbled upon was telling prospects what was bad about his product right off the top before they even asked.

Most prospects said no to Tim. He dealt with enormous rejection and had his ass handed to him regularly by the smart suits working for his competitor EMC. You’d think Tim would’ve hated this job.

But he loved it.

Getting rejected daily eliminated his fear of rejection. It began to feel normal for him so he’d just shoot his shot and see what happened.

The lesson is simple: the people who don’t see themselves as salespeople don’t practice the art form, therefore, they become fearful of rejection.

Let social media do the selling for you

Many people are great at what they do. They have a lot to offer.

The challenge is nobody freaking knows. They’re a ghost. You google their name and nothing comes up. Or a LinkedIn account shows up that has no career history and has done nothing since 2005.

Prospects don’t generally turn around and suddenly go “I’m going to blindly trust you even though I don’t know you.”


Prospects say yes after many interactions. Social media is how you stay top of mind and slowly build trust.

Then when it comes to decision time the prospect feels like they already know you, even though you may have only met them a few times.

Let social media show off your value and do some of the selling for you.

Add this for 3x the results

Social media is level one. Writing a book is level two.

It’s something that shows your value in a different way. A book can even act as an unofficial resume full of references for prospects, too.

Use this strategy to get fast replies to your DMs

Lots of people send DMs (direct messages).

They feel smart when they do. They bombard strangers with sales messages but rarely get a reply. Why?

When you send a DM the person on the other end looks at your social media bio and whatever social proof there is.

If you have 3 followers and a SpongeBob SquarePants profile picture, you look untrustworthy.

To save time and avoid being rude people just won’t reply. Then you’ll say sales is stupid and argue social media doesn’t work. That’s a lie.

DMs work when you put in the work.

Spend some time making your online reputation look more legit. Then send your DMs from a social media account with a little traction. Doesn’t need to be 1M followers and 20,000 tweets.

Even a few hundred followers, a clear profile picture, and a well-written bio that says how you help people — are enough to increase how many replies come back.

Indoctrinate a new person into your world

Whatever you sell is your religion.

People have to believe you give a crap about it and believe it works. The best way is to indoctrinate them.

When it’s early in a new relationship with a prospect, send them a concise clever email on your personal philosophy with a personal story.

I do this in my business through a ConvertKit email welcome sequence.

You can do it in a 9–5 job with a simple template that gets sent to new connections. Once they read your story they’ll start to enter into your world. That’s where the magic happens.

Make lots more sales off one sale

An unintelligent salesperson makes a sale then goes back out to the market to try and make another one.

This is donkey work that leads to insanity.

Instead, ask the client that already said yes why they did. Then use the reason they bought to sell more people. Doing more of what works is seriously underrated. Follow the data.

People don’t give a crap if your offer is better

Trying to be better is hard.

When I had an eCommerce business it was way too hard to be better than eBay or Amazon. So I didn’t. Instead, I tried to be different.

Being different is pretty easy. It starts with smashing the labels of your niche/topic with a sledgehammer.

For example, a friend of mine has a construction company. Every time he tried to win a new deal the prospect would say “submit your tender and we’ll see if your price is the lowest.”

That’s the norm in his industry. I told him to ditch the construction label.

So he started telling prospects he does design and sustainability. He works as a consultant on their building project. Suddenly, people stopped calling him a builder so he didn’t have to submit useless tenders anymore.

Embrace your weird self. Use different language and labels than everyone else in your niche. Watch it skyrocket your conversion rate.

Don’t overthink sales. It comes down to this…

Your job in sales is to bring a prospect to a decision.

If they say yes, you make a sale. If they say no, you save time. If they say maybe, then you’ve screwed up and fallen for their excuses.

Get good at helping people make decisions. And if it’s a no, don’t get mad. Noes can become yeses later on if things don’t work out.

A “maybe” person, though, will simply meet a real salesperson who isn’t you and become their sale.

Write down the conversations that lead to big sales

Every now and then you strike gold.

Something you say or do works and it helps a prospect buy from you and improve their life. The challenge is in three months it’s easy to forget what that is. That’s why I write down every conversation that turns into a big win.

Then when I’m making a similar sale again in the future, I borrow sentences from my wins to increase my chances of further success. Some days I use nothing but templates to sell and it works like a charm.

The #1 non-salesperson mistake

Most salespeople sell features and benefits because they want a prospect to use logic and reason to decide.

The thing is people don’t take action that way. We buy when emotion takes over and makes us act. It’s why stories sell more people than factsheets.

Stories tap into our emotions and make us think “I’ve felt like that before too.” As soon as you have that feeling it’s near-impossible to say no.

You’re not selling out by selling

This is a limiting belief many people have.

Selling isn’t sleazy. Asking for money isn’t evil. When you sell a product, service, or idea you’re helping people get what they want. That’s an act of service. That’s a noble pursuit you should be proud of.

Dan Koe said it best:

People that have a bad relationship with money get trapped in a brutal worldview.

They hate people that sell a product…

Just to work for a massive company that exploits its employees to sell a product…

And never realize that to get out, you have to sell a product.

Memorize these basic reasons people buy

Selling bullsh*t is the biggest reason why members of my private community occasionally fail.

The invent some idea that’s out there and then get frustrated when no one buys. We don’t spend our money or time easily.

The easiest ways to get people to buy are by helping them:

  • Save time
  • Use less of their own effort
  • Make money
  • Get healthier
  • Be better in their relationships
  • Further their career
  • Remove pain
  • Skyrocket pleasure

If you’re doing none of those things, you’ll likely sell nothing. If you’re doing all of them, you’re doing none of them.

Get clear on the human benefit.

The more you talk the less you sell

Some people talk way too much, so the prospect doesn’t feel heard.

Rainmakers in sales talk the least amount possible. They’re not focused on their offer or product. No. They’re focused on knowing the most about their prospect as possible so they can help them better than anyone else.

Less talking, more listening. Quiet people build deep relationships.

The better you get at selling the less new deals you need

There’s nothing worse than a desperate person.

Some salespeople sound desperate because they’re a junkie looking for their next hit. You can see it in their eyes.

But once you get better at sales the money and success you get means you’re not so dependent, therefore, you can sell more.

This makes you come across as carefree and that, bizarrely, leads more people to want to buy from you. That’s how you make it rain money.

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