From Broke Trainer to Seven Figures. Here's What Actually Changed.

In 2016 I made $9,000. The whole year.

I was 26. Just back from a six-month deployment. Working as a personal trainer in California, charging $200 a session, scraping together rent. My W-2 that year was less than what some people spend on a vacation.

In 2025 I made just under $295,000.

That's a 32x increase in nine years. On a W-2. No inheritance. No exit. No course I bought from a guy on Twitter.

I'm not telling you the numbers because they're impressive. Plenty of people make more. I'm telling you because most personal finance writers skip the climb. You get the polished retrospective from someone who already made it. You don't get the broke years.

Here are mine.

There's no shortcut hidden in that list. Nine years of slow, deliberate climbing, with a family that grew underneath it.

I spent my early 20s as a personal trainer. Built a small business doing it. Two online trainers under me at one point. Nutrition counseling. The whole operation looked legit on paper.

In reality I spent every dollar that came in. Income was lumpy and unpredictable. Great month, felt rich. Slow month, panicked. No savings. No investment account. No idea what a Roth IRA was. I was the cliché. High energy, broke as hell, confused effort with wealth.

I joined the Air National Guard at 22. Part patriotism. Part structure. Part paycheck and benefits. The Guard didn't make me rich. It did three things that mattered more.

It put me around people who showed up on time and didn't make excuses. It forced me into systems (fitness tests, deployments, leadership schools) that taught me what discipline actually means. And it paid for school.

I deployed in 2015 for six months. Came back with a few thousand dollars saved. The first real money I'd ever held. I made the only smart move I'd made in years: I didn't blow all of it. Used part of it to start digging out, blew the rest on a truck and a dirt bike, ended up in credit card debt within six months. That's a story for another article.

By 2017 I was 27 and finally serious. Had an associate's from a California community college and another from the Air Force's program. Transferred to a state school for the bachelor's. In-person was breaking me, so I switched to an online program at a big state university and finished it that way. Made $29K, finished the degree, applied to grad school.

A one-year master's in global business. Same university system. Part-time, online, while starting my first real corporate job.

That's when the numbers started moving.

June 2018. BDR job at a small predictive analytics startup. Microsoft Ventures funded. Base salary $69K. No tech background. No formal sales training. 28 years old. Old by SDR standards. I was making cold calls next to 23-year-olds out of business school.

I lasted as a BDR for two months.

Military discipline plus a decade of selling personal training packages plus a willingness to make eighty calls a day when nobody else would. Promoted to Mid-Market AE in August. Enterprise AE eight months after that. By the end of 2020 I'd hit 110% on a million-dollar quota.

January 2021 I got hired at a much bigger enterprise SaaS company. Salary jumped. OTE jumped. Benefits I didn't understand yet. Including the Mega Backdoor Roth this newsletter is named after. Which I ignored for almost a year before figuring out what I had.

I'll write about that mistake separately. It cost me a lot.

From 2021 to 2025 I climbed. AE. Senior AE. Account Director. Each step a salary bump, a quota bump, deeper benefits. In 2022 I hit 175%. In 2023 I got promoted in line. In late 2024 I moved into Account Director.

That's the W-2 story.

Two more pieces.

I picked up a 1099 contract a few years ago that pays $4,500 a month. Started small. Grew steady. Adds about $54K a year on top of the W-2.

Variable commission swings the year up or down. I don't budget around it. Every commission check is found money. Most of it goes straight into investments.

Combined: about $300K of household income in a normal year, on a single earner, with my wife at home with the kids.

Here's the part most finance writers won't tell you about, because most of them don't have kids yet.

For the first decade of my climb, the goal was the next number. Next promotion. Next quota beat. Next salary bump. I'd hit a milestone and immediately reset to the one above it. The number was always the point.

Our first kid changed that.

My wife had been working full-time. We did the math at the kitchen table. The math worked, barely, if I kept climbing. So I did. She quit her job and came home with our son. A year and a half later we had our second.

Something in me shifted that I didn't see coming. The number stopped being the point. The number became the means to a different point.

Time. Presence. Generational wealth.

I don't mean generational wealth in the trust fund sense. I mean it in the practical sense. The kind of wealth that means my kids don't start at zero. That they don't have to spend their 20s broke and confused like I did. That when they decide what to do with their lives, they can decide based on what they actually want, not what they need to do to make rent.

I want to retire at 47 because I'll be 47 when my oldest is 11 and my youngest is 9. That's the window. Middle school. The years they still want their dad around. I'm not retiring to travel. I'm retiring to be there.

That changes how you think about money. The math is the same. The reason is different.

Net worth is around $1.73M. Most of that is home equity, which doesn't count for FI purposes because we still need to live somewhere.

The number that matters is investable net worth: about $610K. That's the pile that funds the next fifty years.

Cash: $78K. Taxable VOO: $147K. Retirement accounts (401k, two Roths, HSA): $378K. Vehicles: $55K. Liabilities: mortgage of $538K (at 4% fixed, already netted against home equity above), student loan $66K.

We bought our house in late 2022. It's appreciated meaningfully since then in this market. The appreciation is real on paper but not something we count on. Houses go up and down. The investments are the part we control.

We invest about $130K a year. 401k, employer match, HSA, two Roth IRAs, the Mega Backdoor Roth, taxable VOO that auto-buys on the 15th of every month. Set and forget. I'll break the whole stack down in future posts.

Three milestones.

Coast FI at 41 ($1.2M investable). Portfolio self-funds to retirement without another dollar invested. The pressure comes off.

Full FI at 47 ($2.2M). I can actually retire.

Fat FI at 52 ($4M). Real margin. Spending could double and we'd be fine.

The plan is retire at 47 and let it ride to 52. By then both kids are in middle school or older. They'll have a parent at home full-time who actually wants to be there. That's the whole point of the climb.

This is what I'd tell 22-year-old me, in order.

One. Income is the lever. But only if you save the difference. Going from $9K to $293K means nothing if you spend $290K. Compounding doesn't start until your savings rate does.

Two. Discipline scales. Whatever made you good at one hard thing (military, athletics, a craft, recovery) is the same muscle that builds wealth. You don't need a different version of yourself. You need to apply the version you already have to a new domain.

Three. The climb is non-linear and humiliating. I was 26 and broke. 28 cold-calling next to 23-year-olds. 30 with a master's degree making less than friends with no education. None of that mattered. What mattered was being further along than I was last year.

Four. The math beats the feelings. Most of my early mistakes weren't from being dumb. They were from optimizing for what felt responsible (paying off debt fast, holding cash piles) instead of what the numbers said (invest the spread). The math doesn't care how you feel.

Five. Boring works. I hold VOO. I have one mortgage. I drive a paid-off car. I don't day trade. Don't pick stocks. Don't rotate sectors. Almost everything that's worked for us has been boring on purpose.

Six. Your kids are the reason. They're also the deadline. Nobody with young kids and a real job can afford to wait until 50 to figure this out. The work compounds. But only if you start.

Seven. The number isn't the point. The point is what the number lets you do. Most high earners I know never figure this out. They hit the milestone, reset, hit the next one, reset. They're 55 with eight figures and no relationship with their kids. Don't be that guy.

Next week: the moment that broke my "spend every paycheck" cycle as a trainer. The small habit that made everything else possible.

Two weeks out: the Mega Backdoor Roth itself. What it is. How I missed it for almost a year at my own company. What that mistake actually cost me.

If someone you know would find this useful (high earner who feels behind, parent trying to figure out how to make this work, veteran trying to figure out the financial side, personal trainer or service worker grinding their way up), send them to themegabackdoor.com.

Same time next Tuesday.

Cole