Money: What I've tried, what failed, and what I learned. Ever

Recently I watched a peer announce publicly that he had failed at real estate and was quitting. I think/hope he was just venting but it did make me reflect on how many different ways to make money that I've tried, failed, and quit along the years.

Failure is an inevitable part of the adventure of life, and in my case it's been mostly failure.

The Army

I was a descent soldier but as you can imagine the military was too rigid for me. No financial upside and a lifetime of bureaucracy? Thanks anyway.

Selling cars

I was pretty good at selling cars.

Learning sales was a valuable skill and selling cars is interesting because it's one of the few jobs I know where you can walk onto a car lot anywhere in the united states today and pretty much any of them will give you a shot. They provide all the inventory and marketing, all you have to do to make a living is show up and be nice to people.

The problem with car sales is the same as the benefit: you own none of the inventory and none of the marketing, there is no advancement in the industry, and it's full of month-to-month thinking people.

I got fired from this after getting a DUI, which ended up changing the course of my entire life. If I hadn't made that error I might still be doing that. Glad they fired me.

Building houses

My uncle asked me to come to Arizona to build some houses with him. I learned that houses are not as complicated as I thought and I'm terrible at working with my hands. He didn't pay me much but based on my talent and interest in the work I was still probably overpaid.

Grosource

My first "entrepreneurial" endeavor. Started by my buddy Johnny Robinson, who I love forever, started this company and it was sort of like an early meetup.com. He saw a lot of potential in me and I was excited to participate.

To this day, I still can't tell you what Grosource was (or is, I think he is still tinkering with it 20 years later). The idea was that a bunch of local business would give customers discounts for cross shopping and would cross advertise for with each other.

I did this for about 18 months, we made no money.

Roof Dawgz

This was a door to door roof replacement sales gig that a friend hired me for. Very small business, only 3 people, I thought I could grow here. This is not a bad business, but I don't think I'm cut out for door to door sales. The guy who I was for on this wasn't really turning it into a business he was just living on the income and had no intention of scaling it, so there was no clear future here for me.

Retail banking

I got my bachelor degree thinking "I'll get a 'real job' and get some stability. This sort of worked but I was making $45k/year in my mid-30's and still had no assets to show for myself.

This is not how I hoped my life would turn out.

This was fairly stable but this was another sales job in disguise. I was tasked to cold call bank customers to solicit them to sign up for credit cards and small loans. It was also a regional bank in a small town. I looked at the future and if I really worked hard and got promoted and made a career of this there was still not a 6 figure income anywhere in the future.

I realized I needed to own something.

Single family rentals

In 2013 the foreclosure boom was happening and I had almost no money but I needed almost none to buy a small piece of real estate. I spent 9 months learning everything I could about real estate and moved into a 55k foreclosure with 4k out of pocket.

I spent the next 18 months doing slight renovations with mediocre work (thanks to my uncle for teaching me how to build houses) and it appraised for 115k.

I was 35 and this was the first time I had ever made what I considered real money.

Small business risk analysis

I moved to Las Vegas, and got a risk analysis job for a commercial bank. I was still only making 55k a year. I lived here for 3 years and spent most of my time buying rentals back in that small town, as I got good at it I thought I could move back and scale up....

Flipping houses

I flipped 4 houses over 2.5 years, probably made less than 50k total, and I hated it. Flipping houses works at scale, I don't think it's good to do as a hobby. To create a constant source of deals, contractors, and funding at scale, you really need to like project management. Since houses are very illiquid and the cash conversion cycle is long, exits are very market dependent, and the entire business runs on short term debt, it can theoretically blow up on you at any time. That sort of anxiety plus a type of work I didn't like scared me off quickly.

Multifamily apartments

Scale is always better right? I purchased a 24 unit apartment complex in 2019, and a 52 unit in 2020 (which I still own). The 24 unit sold 24 months after owning and I paid my investors a 50% return. The 52 unit has succumbed to the market downturn that all multifamily has experienced and it's sort of just slogging along.

I realized that large multifamily is little more than an interest rate hedge. Can you get great deals? sure, but for a large percentage of the transactions the goal is to buy at a large cap rate and sell at a lower cap rate. If you do the reverse, you can lose all your money.

Since cap rates are dependent on interest rates, the operator is in less control of the outcome than I would want considering I'm investing other people's money. Additionally, the operator mainly gets paid during the exit, so you work on these deals for 5 or 10 years before you find out if you're going to make any money.

There are areas where I still like this asset class, but this was not a great revenue generating activity for me.

Life and Lens

I had been a hobbyist photographer for a few years and I was getting good. In 2020 people started hiring me for work and I thought I could make some descent money here. Freelance videography is extremely labor and emotionally intensive. Everything I made was a reflection of myself, if someone didn't like my work, I took it personally. This is not good for business.

Also, business owners don't want art - they want outcomes. What I should have done instead was learn marketing with a small bit of videography.

I did learn that I love my camera though, I will be a photographer for a very very long time. Money or not.

Betterlife

The camera did get me some cool places.

Brandon Turner invited me to move to Maui and help him build a video podcast and private community called Betterlife. I knew this was going to either blow up good, or blow up bad.

It started off strong, he paid me the most I had ever made, we had a great time, but it was short lived. Unfortunately Brandon spent every single dollar that company made, which meant no matter how well it did it was always on the brink of ending. I was fairly displeased with what I considered to be mismanagement and I really didn't like living on the island anyway, so I departed. I think Betterlife still exists but he lost most interest in this project before I was even gone so no love lost.

War Room

My buddy Dave started a private community for veterans a few years back and as it grew he needed to hire people, I came in to help at an extremely small income and spent the last few years increasing my value. I currently work with Dave and make a reasonable salary, though nothing to brag about.

Thankfully, I absolutely love this work

The Beacon

I love people, I love events, and I am a self diagnosed conference junkie.

The problem with conferences though is that I don't care about all the hype and the stage and the speakers, I just care about bonding with people at the bar. So I tried to get people to come to Austin and do small workshops to recreate that experience.

The problem with this model is that it's very difficult to get people to leave their house and fly across the country. This works if you have a very big audience and very clear outcome to promise.

I still do an international Beacon trip each year and I will probably continue to do 1 of these, but not for profit, and only if it's low effort.

Day Trading

In 2025 a friend who is a full time day trader convinced me to give it a shot. I spent 6 months learning this process and it was enlightening. With prop firms you can essentially day trade with zero of your own risk and make real profits. I consistently watched him make 20-30k months without using his own money.

This was real

However, it is also an emotional nightmare that I personally can not handle, and very few people can. I could tell that it would take me 2-3 years of being glued to a computer ~5 hours a day watching charts before I would be able to consistently turn a profit and even when I did there was no way to outsource/scale it.

Quilt shop

All praise to my Miss Kate.

In 2024 she started an online quilt shop that sells quilt fabric to quilters. I have been blessed to be part of this because it's allowed me to use my innate talents to their maximum and the quilt shop fixes all the problems that every previous project had.

(I would like to point out that I have not personally taken a single paycheck from the quilt store and it's not likely that I do so for a few more years.)

It's too soon to tell, but the quilt shop might finally be the thing that makes us real money. While the vast majority of the work and sales are done by her, I have been able to help in ways I never expected. I've learned how to run a Shopify store, how to do email marketing, how to run paid meta ads, how to properly run financial infrastructure, how to find us a warehouse to move into when we outgrew our space, how to find and hire staff, how to train staff, and how to do product photography.

Lessons

I'm just about to turn 43, I have no real career, and as you can see I have a very long list of projects that have not worked out. Are these failures? of course they are. The question is what did I learn from them that I can give to you.

Life is unfair and many of us figure things out late in life. I also know that I really only have to win the money game ONCE to make up for all these failures. Also, if you learn from failure and keep trying you keep getting chances to win.

Here are a few things I learned from all this mess:

Financial discipline

Despite rarely making over 50k/year in my entire life, and starting my early 30's with a negative net worth, I've been able to build a muli-million dollar financial portfolio in just the last 10 years.

Whatever you do, learn financial discipline.

In 2013 I decided my plan B would be to invest slow and steady and safely in case I fail at everything else. More than anything else I've done, this has worked.

If you can sacrifice your lifestyle today to put capital into the stock market or a piece of real estate and just hang on, you will get wealthy.

Conversely, if you are bad with money you will destroy all the money that comes to you no matter how much you make.

Skin in the game

You have to put your money and your labor into your own projects. Without skin in the game you will not care enough about the outcome to work as hard as you need to or avoid risk you're supposed to. You will never truly learn the lessons you need until you carry your own risk or know the wins were on the back of your own choices and resources.

Entrepreneur or Investor

The investor wants to go slow and cautiously, the entrepreneur wants to go fast and break things. They are much closer to being opposites than they do overlap.

Know which game you want to play, and know which of these is required for the game you're playing.

Real estate makes these two things very grey, and that makes many people's lives painful.

(Almost) Everything works, everything is hard, pick something and learn from doing

Almost everything on this list could produce all the money I ever needed. I quit on them because I either didn't want to do that type of work, I didn't believe in the team, I wasn't good enough, I didn't want to solve the next hurdle, or I wasn't the owner of the outcome.

No matter what you do it will be hard, it will take longer than you want, you won't be sure it will work, and it will not be perfect. You think I wanted to start a quilt store?

Don't climb two mountains

If you try and do 2 or 3 businesses at the same time you won't succeed. I've tried this many times, and I've seen everyone try it. It doesn't work.

Pick one thing, burn the boats, and go all in, don't change your mind for at least 5 years. I've wasted so many opportunities but bailing too soon hoping the next thing would be easier/better.

Very clear value proposition

If you cannot explain what it is or what problem it solves in a sentence. Don't bother.

Don't build an idea. Build revenue.

Ideas are useless. Too many people, myself included, have and continue to build businesses that have little or no revenue. This is a tragic error

Sell something immediately, listen to the customer, iterate the process. Once you have a good number of repetitions of the process (sales+fulfillment) and you think you will be good at doing more, then you scale.

You must have leverage

The quilt shop serves the entire united states from one website. Leverage

The quilt shop can talk to millions of quilters with one instagram channel. Leverage

Freelance photography always requires me and what I provide is custom for every client. No leverage.

You need something you something where you can talk to your customers at scale and deliver at scale. If you insist on doing it custom, it has to be incredibly expensive and you still need to talk to your customers at scale.

Low or no debt

Real estate is a ton of debt. I'm not opposed to debt, but it's appeal to me has grown soft over the last few years. Debt is risk, full stop.

Maybe your experience in business will be different, but as you can tell from the list I've given you, success is not a guarantee. Do you want to add leveraged risk on top of this process?

(Disclaimer, I still have a ton of debt on my real estate and I'm not planning to pay it off anytime soon, but the quilt store has no debt nor will it ever).

You don't have to be passionate about it, but you can't feel icky

I used to say "I just want to sell something I love" and I have lessened my opinion on this. I won't sell anything that I think is gross - which admittedly is many things (most forms of brokering, courses, coaching, and other things without skin in the game) but there are a lot of ways to make money that are just good business and don't have to be more than that.

I think in the past I was trying to make my business serve too many needs. I needed it to be my passion, my grand purpose, it needed to fit all my specific talents, and it needed to be profitable. I think now I've matured enough that business can be business and my self worth doesn't have to be wrapped up in it.

How does this compare to you?

I'm curious what 10 year from now Alex will say when he looks back on this? Will these lessons stand true, or will I change some of them?

How much will I fail in the next decade? More or less than previously? More importantly, if I fail across the next decade, will I continue trying?

How does my history and these lessons compare to your experience?