Own Your Upside

Hosted by Aaron Ameen

Business InvestingInterviews guests

Website RSS feed LinkedIn YouTube

Episodes

160

Latest episode

Oct 2026

Language

About the show

You've done everything right. Good income, career momentum, a family worth protecting. Underneath, a quiet realization: the path you're on is optimized for someone else's outcome. For high-earning professionals ready to build ownership alongside their career, before later costs them the years that matter most. I'm Aaron Ameen. I built a multi-state real estate portfolio while working full-time with three kids under four. Now I'm developing Everwood Reserve, a $10M assisted living project, while writing a book and building a coaching practice. The build, as it happens. Stop renting your upside.

Listen to episodes

60 recent

October 2, 202645 min

How Real Estate Made Getting Laid Off the Best Day of My Life

My friend Zach Metcalf spent 10 years in pharma, making around $400K a year. On February 12th at 9:15 AM, his boss told him his position had been eliminated. After a decade with the company, he had 30 minutes to wrap up and leave. Instead of panicking, he celebrated. For eight years he'd been buying real estate on the side, starting with a house hack and one rental in Joshua Tree. By the time that call came, his portfolio was bringing in $10K to $12K a month and covering his family's expenses. He walked away with a $61K severance, and 31 hours later his wife landed her dream job. We talk about how he built that income while working full time and why he stayed for the severance instead of quitting. He also shares what the first months without a paycheck actually felt like, including the burnout that hit five months in. If you're in a job you've stopped believing in, Zach's story shows what being ready for that call actually looks like.

September 16, 202625 min

Why We Kept Our W2 Jobs For 7 Years While Building

Andrea and I started buying real estate in 2017 and I did not leave my job until earlier this year. Seven years. That was not slow, it was on purpose. In this conversation from the Pending and Trending podcast with Deidre Quinn, I get into why we built in parallel instead of quitting, the question almost nobody answers when they set a cash flow goal, and how one rental property we underwrote badly in 2019 led us to the $9.4 million ground-up assisted living development we are building in Texas right now. We also talk about the part of the story I do not lead with often. I got out of rehab for alcohol abuse in May 2019 and bought our first rental two months later. That was not a coincidence. It was the point I stopped blaming my employer and started looking at the trade I had agreed to. If you are making good money and quietly aware that you are creating more value than you are capturing, this one is for you.

August 1, 2026Episode 559 min

How to Completely Transform Your Life in 3 Years w/ Brian Luebben

Three years ago I was buying rentals twenty minutes at a time after my daughter went to sleep. I had a good job, a decent portfolio, and no real answer for when any of it would add up to something. My mentor Brian Luebben has walked thousands of high earners through the same gap. In this episode he gives real timelines for what it takes to replace your income depending on the path you pick. We also get into the call where he told me not to quit, and why the order you do things in matters more than how fast you move.

July 23, 2026Episode 67 min

High Salary, Big Title, Zero Ownership: The Trap Explained

I left a six-figure consulting job in January. Not because I quit on corporate. Because I finally saw what my title was actually costing me. In this episode I break down: 1. Why a title proves you created value, not that you kept any of it 2. The math behind why a 3% raise quietly puts you further behind every year 3. Status as a currency employers pay you in, and why it's not the same as ownership 4. The one shift that turned my paycheck into a tool for building real assets, not just a way to survive This isn't another "quit your job" video. My wife Andrea and I built an eight property rental portfolio and a ten million dollar assisted living development in Houston while I worked full time the entire way through.Grab the free worksheet in the link below and run your own numbers against the three questions in this episode. Next up: the exact number that told me it was safe to finally leave. Here is the worksheet: https://worksheets.ownyourupside.com/title-cost-audit Want a shorter version too, for cases where the platform truncates descriptions?

July 16, 202653 min

He Ran the Numbers on His "Stable" Career. Then He Left.

Most people making good money have never run the actual math on where their career ends. Not their savings rate. The terminal number. What all these years of work actually produce when the working stops. My guest today did that math at 35, standing on a ladder next to a 63-year-old electrician with a three-year-old son. The man’s pension after 20 years on the job: $2,000 a month. Luke Gilbert quit the union within four months. In this episode, Luke walks me through every reinvention that followed. Sound designer, bartender, electrician, Rookie of the Year real estate agent, performance coach, and now founder of an AI employee company for real estate professionals. Four kids drove every pivot. We get into the questions I think about constantly. Whether a W2 is an asset or just a stepping stone. Why building alongside your career beats waiting for permission. Why process has to come before systems. Why you can’t leapfrog experience, even with AI. And why the ability to pivot matters more than any single skill you’ve stacked. If you’ve been doing everything right and still feel like you’re getting nowhere, this conversation is for you. Find Luke on LinkedIn: Luke W. Gilbert.

July 10, 20267 min

How I Quit My Job Without Gambling My Future (The Exact Number)

Stop gambling your financial stability to build something new. Learn the escape velocity strategy to scale your income and skills safely. Many professionals are told to quit their jobs and take huge risks to succeed, but this approach often leads to unnecessary failure. This video breaks down why abandoning a stable situation is rarely the best path and how you can achieve significant career growth while keeping your foundation intact. We explore how to apply the escape velocity strategy to your own life by focusing on high-value skill development and financial growth. By prioritizing these two pillars, you build a sustainable path forward without the dangerous volatility associated with traditional startup advice. This method is designed for those who want to advance their careers or personal projects without sacrificing the security they have already earned. Subscribe for weekly career and finance strategy breakdowns, and comment below: what is one skill you are currently developing to increase your long-term value?

June 25, 202612 min

Why Your 3% Raise Is Keeping You Poor

After 150+ episodes, I'm launching a new chapter. In this one I share why my "successful" W-2 life and a solid rental portfolio still left a gap and why my wife Andrea and I sold properties to build a $10M assisted living development. This is the launch of Own Your Upside: how I'm building in parallel, 20 minutes a day, until the day job becomes a choice instead of a requirement.

June 11, 202628 min

The Real Estate Crisis Nobody's Talking About (Until It's Too Late)

Most real estate investors are chasing cash flow. We're building for a problem that's about to reshape the country. My wife Andrea and I left a portfolio of single-family rentals to develop two luxury assisted living and memory care homes in Houston. The reason is simple: the population is aging far faster than we have the capacity to care for them, and once you see that gap, you can't unsee it. In this conversation, recorded at Michael Zuber's One Rental at a Time event with Matt the Lumberjack Landlord, we get into: — Why we walked away from traditional rentals for ground-up senior care development — The lease-to-operator strategy that bridged us from rentals into this space — How we de-risked a first-time eight-figure development through zoning, market analysis, and team — The bank that pulled out five days after we closed our raise, and what we did next — Why we believe this asset class will endure whatever the market does If you're a W2 professional looking for a path with real demand behind it, this is the thesis in full. EVERWOOD RESERVE everwoodreserve.com

May 28, 2026Episode 145 min

How We Built a $9.4M Project Before Quitting Our Jobs

Most people quit their W2 to start building. We did it the other way around. My wife Andrea and I raised $2.8M, broke ground on a $9.4M senior care development, and built our entire team before I ever handed in my notice. This is what the Parallel Build actually looks like in practice. In this conversation: - How we went from 8 single-family rentals to a $9.4M ground-up development with no prior development experience - The team architecture that made a first-time eight-figure project lendable - What the $2.8M capital raise really looked like, including the bank that pulled out five days after we closed - How Andrea and I aligned our vision as a couple on a project this size - What it actually feels like to build something at this scale when the math is against you If you're a W2 professional trying to build something real on the side, this is the full arc.

March 19, 20266 min

Your Investment Goals Keep Stalling (And How to Fix It)

You’re ambitious. You want to build wealth. Maybe that means buying your first rental property, launching a business, or pursuing a bigger project. But here’s the reality most high-performing professionals face. Your calendar is already full. Between work, family, and everything else life demands, there’s never a clean block of time where you can just “focus on the big thing.” So most people stay stuck in planning mode. They read books. Listen to podcasts. Analyze deals. But the big projects never actually move forward. Today I’m going to show you the quarterly planning system I use to make meaningful progress on big projects without burning out or sacrificing the parts of life that matter most.

Is this your show?

Claim this listing to keep it up to date, reach guests who want to pitch you, and manage bookings with Guestify.

Claim this listing

More Business podcasts

The Bottom Line

Alexander Spencer

BusinessInterviews guests