I worked for a 20 something millionaire

Here's what I learned:

At 24, my monthly income surpassed my annual income at 21.

my bedroom Jan, 2024

And it’s mostly because I took a sales job for a well-known writer.

In the beginning, I was terrified I would fail because I had no sales experience. And I nearly did. But then I went on to sell millions of dollars for the company and learned a lot.

The best part was, when I worked there, there were no managers. My direct mentor was the founder. And because he’s someone a lot of people look up to, I was eager to learn from him.

That’s why I took the job.

Now beyond how to sell, here are some things I learned from him as our mentor:

1. The power of agency

Agency means owning your outcomes.

A high agency person is someone who is intentional and focuses on the things they can control to get their desired outcomes.

Being high agency starts with deciding clearly what you want. Low agency people drift. They are unintentional and blame things outside of their control.

One of our first principles as a team was extreme ownership and absolutely zero complaining or blaming was tolerated. That allowed us fix mistakes quickly.

Once you work with high agency people, you can never go back.

2. The EOD rule: how you can shorten your time horizons

We had a saying about getting things done:

• “End of day not end of week”

This completely transformed our way of operation. When your default state is to finish things within 7 hours instead of 7 days, you literally make 7x the progress over the year.

You may have heard of Parkinson’s law.

"work expands to fill the time available for its completion"

It’s a productivity rule that states the length of a project will expand to the time allocated. Everyone knows this from school. You wait til the last day of a 3 week assignment to write your essay.

So if you want to make more progress, make your default end of day, not end of week.

3. The perceived value of “facetime”

The founder gave us weekly 1-1 coaching calls.

They were not like sales coaching. They were like life coaching. And even though I often knew the advice he would give me (based on his writing or mentality), it’s hard to explain how much harder a lesson hits when someone you respect tells it to your face.

I also noticed the inverse of this.

We were selling a group coaching offer. And some people bought because they wanted that direct access to the founder. But the reality is the only way to scale a group coaching offer is to limit access to the founder.

The highest agency students had no problem with this and took action anyway. But one or two people told me they wished this had been different.

People seem to perceive 1-1 advice as more valuable than 1-many advice, even if it’s the same advice.

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Costly signaling rule:

I believe the famous marketer Rory Sutherland talked about this before.

There is something about the “costly” signaling of how you deliver information that either amplifies or diminishes the impact.

If you’re American, you know how much effort people put into their Christmas Cards. And it’s touching to receive them. Or in the business world, if you FedEx overnight something, it immediately seems more important than if you text the same exact thing.

Packaging and framing changes perception of value.

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4. How I bounced back from a terrible start

Even though I helped the company make millions, I failed to close most live calls.

A 31% close rate still means 69% said no.

And it’s hard to not take the Ls personally. For the first two weeks, every call felt life or death. And I had horrible commission breath. (a joke for when you are dying to close deals and you “stink” to the prospect lol).

You start to realize over time, feedback over failure is the more useful frame.

Have a terrible call? Prospect hangs up on you? Get called pushy?

Good. All data points for what not to do next time.

Everyone knows it’s better to maintain openness to truthful feedback. Detachment from immediate outcomes helps you do that.

5. The million dollar compound experience

The founder recommended we live together to learn more.

So I moved in with the top sales guy.

At first it was just him and me. Then we moved into a penthouse with the newest sales guy. We worked day and night. Closing deals. Coming out of our bedroom smiling or agonizing depending on the outcome of the call. Eventually two more guys moved in.

Sometimes it was so packed that we had people taking sales calls in the living room.

We called it the “compound” as a joke:

View from our roof

But it was literally a million dollar revenue center for the business. Two of us then got girlfriends in the building. Our entire life was in the compound.

Looking back on it, it was hilarious.

But the reality is we were working extremely hard and sometimes extremely long. And having friends for the ride made it bearable and extremely fun.

People joke about whether it is the journey or the destination but I’m starting to realize the company is probably top of the list for me.

6. Why making more didn’t make me happier

Because of this job, I became a top 1% earner for all 24 year olds in the United States.

But I still felt like shit sometimes because I watched my boss make my yearly income month after month, and Miami kids in Lamborghinis on Instagram, and I spent too much of my income to feel a significant sense of security.

It’s super easy to get lost in the sauce of seeing people ahead of you.

The reality is, if you are working a job, even a very well paid job, it will be hard to make as much as the business owner who leverages people, processes and systems to create scalable earnings.

And sometimes you are in a learning phase to get ready for that moment to strike in the future. And that’s ok.

That’s all for today.

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Thanks for reading.

Please let me know if you would like to hear more about the lessons and funny stories we have from helping to scale a multi-million dollar sales team.

Thank you.