The Tesla Engineer Who Bet on Tesla Stock Options—and Mapped His Way to Freedom

Not Your Typical Tech Bro

You ever meet someone who just gets it?

Like, not in a “they went to all the right schools and wore Patagonia vests to networking events” kind of way. More like… they looked around at the world, said “nah,” and then built something smarter from scratch?

That’s Jarred.

From Industrial Grit to Tesla Giga Grit

Jarred used to work at Tesla. Before that, he was deep in the industrial automation world—Rockwell, coal plants, natural gas stations. Basically, stuff that felt like the past. And he knew it.

So he bailed.

Did some quick research on Tesla (dude hadn’t even followed the EV space, which makes this even more impressive), took the job, moved to Nevada, and jumped in right as Gigafactory Nevada was getting off the ground. Back then, there was one production line. One. They were cranking out Powerpacks like it was the early days of some garage startup… but with giant robots.

Becoming the Machine Whisperer

Jarred didn’t just clock in and zone out. He showed up with all this experience on PLCs and legacy equipment and basically became a wizard on the sustaining team—making ancient California scavenged machines talk to Tesla’s shiny new systems. Picture Doc Brown fixing up a DeLorean using parts from a fax machine and a spaceship. Yeah, it was kind of like that.

Stock Options? All the Tesla Stock Options, Please.

While most people at Tesla were playing it safe with their Tesla stock options—grabbing RSUs like they’re free samples at Costco—Jarred looked at the recruiter and said, “Give me all the options.”

Not some. Not half.

All. The. Options.

Recruiter was like, “Wait, seriously? No one does that.”

And Jarred? Cool as a cucumber: “If it works, I win. If it doesn’t, I’ll be looking for another job anyway.”

Figuring It Out—One Spreadsheet at a Time

Thing is, nobody at Tesla really sat the employees down and explained how all the stock stuff worked. No “here’s how taxes on ISOs hit you like a truck.” No “hey, AMT is a thing and you might wanna plan for it.” So naturally, people started huddling up at lunch, pulling out spreadsheets, comparing notes, and trying to reverse-engineer their way into not screwing themselves.

When DIY Meets Diminishing Returns

Fast forward to late 2022. Jarred’s nearing his Tesla exit and realizes: “Alright, I’ve taken this DIY thing pretty far, but I’m gonna need some help if I’m not trying to hand Uncle Sam my entire portfolio.”

So he calls up Bradford and the Rebellionaire crew.

Why? Because every other financial advisor was like, “Hmm, concentrated Tesla stock? Scary! Let’s diversify you into 14 different funds we manage. Also, we’ll take a nice fee, thanks.”

Nah. Jarred didn’t want that BS. He wanted someone who actually understood Tesla. Someone who wouldn’t flinch when he said he was staying all-in. Not because he was reckless—but because he believed. In the mission. In the tech. In the upside.

The Plan That Saved His Upside

So together, they mapped out a legit game plan: how to exercise options strategically, when to use margin (and when to not), how to minimize taxes, and how to actually hold onto shares instead of panic-selling every time the media screamed “Volatility!”

Real talk: margin gets a bad rap. But used right? Like, Jarred-right? It’s just another tool. They used it to avoid forced selling, trimmed when the stock hit $350, paid off the debt, and walked away in a stronger spot. The guy literally avoided a massive tax trap, timed his sale after the stock surged, and got to keep more of his hard-earned upside.

It Wasn’t Luck. It Was Conviction.

Could’ve gone sideways, sure. But it didn’t. Because he understood the risk. Because he had backup. Because he stayed engaged, asked the right questions, and didn’t let fear (or random suits from Fidelity) talk him into dumping Tesla.

Jarred’s story is wild not because it’s some lottery-ticket fairytale—but because it’s what happens when you go all in on conviction, learn every single inch of the system you’re playing in, and then find a team that actually respects that vision.

Most people play defense. Jarred played offense. And not the reckless kind. The kind where you’ve done the math, looked at the tech, and bet on the future… because you built part of it.

The Difference Between Riding the Rocket and Steering It

And if you’re sitting there holding a pile of stock options, trying to Google your way through tax hell, just remember: there’s a difference between riding a rocket and actually knowing where it’s going.

Jarred? He brought a map.