I Outsold the Entire Sales Team. Then I Quit.

The insurance underwriter who humiliated his sales team, then walked out to build a rental empire (and why your "safe" job is the riskiest bet you'll ever make)

Most people think Path A costs them time and money.

They're wrong.

Path A costs you something far more valuable: Hope.

Let me tell you about the day I learned this lesson the hard way.

(And if you're one of those people who thinks they already know everything about building wealth because you maxed out your 401k, feel free to schedule a reality check session here → where I can show you exactly why you're still broke. The rest of you, keep reading.)

The Breaking Point That Changed Everything

I was working as an insurance underwriter, and I knew—absolutely KNEW—I should be in sales. I had the skills, the drive, the results to prove it.

But there was one problem: I didn't have a college degree.

The company had this "requirement" that salespeople needed college education. Never mind that I could clearly do the job. Never mind that sales was obviously my strength. The piece of paper mattered more than performance.

Now, I'm not here to bash college entirely—it has its place for certain careers. But using it as a blanket requirement for roles where it's irrelevant? That's just gatekeeping disguised as standards.

Here's where the story gets interesting.

They ran a contest: underwriters vs. the sales team. Who could sell more of a particular policy during the contest window?

I saw my opportunity.

Not only did I outsell every single person on the sales team, but I helped every other underwriter sell more too. We won as a team, proving beyond any doubt that the "college degree = sales ability" equation was complete nonsense.

And then? I quit.

Walked right out after we won to make my point crystal clear: You just lost someone who could outsell your entire sales force AND teach others to do the same.

But here's what that experience really cost me...

"It Cost Me Hope"

For years after that, I was angry. Furious, actually.

Not because of the job itself. Not because of the money I missed out on. Not even because of the petty manager I didn't get along with.

I was angry because nobody had told me there was another path.

If someone—anyone—had shown me that there were other ways to create value besides trading time for money as an employee, I would have chosen differently from the beginning.

That's what Path A really costs you: the hope that there's something better out there.

Path A convinces you that your only options are:

• Find a "good" job

• Work hard for 40+ years

• Hope your 401k and Social Security will somehow be enough

• Cross your fingers that nothing goes wrong along the way

But here's the truth your parents, teachers, and guidance counselors never told you: Jobs aren't secure. They're actually one of the most insecure things out there.

A job is a single point of failure by design. And it's not designed to make you financially literate or teach you how to build real wealth—that's not what it's for.

So what's the alternative?

My First $200 That Changed Everything

June 18th, 2008. (I just realized this anniversary just passed as I'm writing this.)

That's the day I closed on my first rental property: a single-family house at 596 Flores in San Bernardino, California.

The passive income? A whopping $200 per month.

I have never—and I mean NEVER—worked so hard for $200 in my entire life.

But here's the thing: I wasn't really working for $200. I was working to prove that I could do it. That this "Path B" thing was real and achievable.

I even created a rule for myself: I wouldn't buy the $20 iPhone update (this was back when updates cost money) unless I could pay for it with passive income.

$20. That's all I needed to "allow" myself this tiny purchase. But I refused to use active income for it.

When I finally closed that deal and got my first $200 passive income payment, I went and bought that iPhone update with the biggest grin you've ever seen.

Because in that moment, I understood something profound:

Once you understand how to create value and live off the income of assets, you can go anywhere in the world and create value—literally anywhere, even if you don't speak the language.

There's a peace and comfort that comes with that realization that no job can ever provide.

The Two Paths: A vs. B

Let me be clear about what I mean by Path A and Path B, because this distinction will determine the trajectory of your entire financial future.

Path A is what 95% of people follow:

• Trade time for money

• Work for someone else's dream

• Hope external systems take care of you

• Accept whatever "security" you're offered

• Retire when someone else says you can

Path B is what the other 5% figure out:

• Build assets that generate income

• Create systems that work without you

• Control your own financial destiny

• Generate multiple streams of income

• Retire when YOU decide you're ready

The difference isn't just financial—it's psychological, emotional, and spiritual.

Path A people spend their whole lives worried about layoffs, economic downturns, and whether their retirement accounts will be enough.

Path B people sleep soundly knowing their income comes from assets they own and control.

The Hard Truth About "Security"

Here's what nobody wants to admit: Your "safe" job is lying to you.

Every two weeks (or twice a month), you get trained like a lab rat. Show up, do the work, get the deposit. Don't show up, don't get paid. Simple, predictable, "secure."

But Path B doesn't work like that.

You get up, put in the energy, and it might be WAY more than two weeks before you see results. Once the asset exists, you're still not done—you have to learn how to sell the use of the asset, not the asset itself, which takes even more time.

But here's what happens next: That asset continues to produce results over and over and over again.

This is delayed gratification in its purest form, and most people simply can't stomach it.

They want the deposit every two weeks. They want the immediate reward for immediate effort.

And that's exactly why they'll never experience true financial freedom.

(Still with me? Good. If you're starting to realize your "secure" job might actually be a financial prison, let's talk about your escape plan →. I have a few strategy sessions available this month for people ready to stop making excuses and start building assets.)

The Path B Challenge

If you're still reading this, you're probably wondering: "Okay, this sounds great in theory, but what's my actual first step?"

When I start working with people, their first Path B step isn't what you'd expect.

It's not finding the perfect property. It's not raising capital. It's not even picking a market.

The first step is overcoming their perception around what they lack.

Someone mentions an opportunity, and immediately we become experts on everything we don't have: "I don't have the money." "I don't have the experience." "I don't have the connections." "I don't have the time."

Here's a reality check: No entrepreneur starts with all the money. But for some reason, we think we need to have everything figured out before we begin.

That's Path A thinking infected in a Path B world.

The truth is, you already have more than enough to get started. You just need to see the opportunities instead of focusing on the obstacles.

What's Next?

This is Part 1 of what's going to be a detailed exploration of Path A vs. Path B.

In the coming parts, we'll dive deeper into:

• The 6 steps every Path B asset must follow (Build→Own→Control→Manage→Grow→Protect→Transfer)

• Why real estate, particularly short-term rentals, is the perfect Path B vehicle

• How to make the mental shift from employee to asset builder

• Real examples of people making this transition (including some dramatic transformations)

But right now, I want you to ask yourself one honest question:

How much hope has Path A cost you?

If you're tired of trading time for money and ready to explore what Path B could look like for your specific situation, I have a limited number of strategy sessions available where we can map out your transition plan.

These aren't sales calls—they're genuine strategy sessions where we'll look at your current situation, identify your best Path B opportunities, and create a realistic timeline for building your first income-producing asset.

Click here to schedule your Path B Strategy Session →

The session is complimentary, but I only have a few spots available each month, and they typically fill up within 24-48 hours of sending these emails.

If you've read this far, you're already thinking differently than 95% of people. The question is: what are you going to do about it?

To your Path B success,

J. Massey

P.S. That $200/month property from 2008? It taught me that the amount doesn't matter nearly as much as the principle. Once you prove to yourself that you can create passive income, scaling becomes a matter of systems and strategy, not luck or magic.

The hardest part is going from $0 to $1. Everything after that is multiplication.

---

Ready to start your Path B journey? Schedule your complimentary strategy session here →