We have always maxed out our retirement accounts. That slow-and-steady process allowed me to reach $500k in my early 40s. Combined with my wife’s retirement accounts we recently passed the one million dollar mark. What allowed us to retire early was the amount we had in our taxable investment account. Here’s some background on how we made our second million dollars.

How We Made Our Second Million

The First Million

If you haven’t already read how slow and steady got me to $500k, you might want to check out that post now. My wife had similar results so between our accounts we were able to recently pass the $1 million mark. If you have a hard time seeing how to hit a million dollars in your personal retirement accounts, check out the postHere’s how much you’ll have if you max out your 401k plan.

As someone recently commented, not everyone makes enough money to max out their retirement accounts. I understand and that’s a very real challenge for a lot of people. Two thoughts on that – yes it does tie into this topic.

1. If you cannot max out your retirement accounts, you might not need to. As shown in the awesome chart over at Early Retirement Charted, what matters more than what you earn is how much you save. I mean, how much you save relative to what you earn. There are early-retirees in their 40s who never earned more than average salaries. A comfortable retirement is possible if that is indeed a priority.

2. The second thought leads to the heart of this topic. If you don’t feel like you are making enough money to save and invest, perhaps you are right. In that case, you might want to consider making more money. I wrote about my experience changing careers so that I can earn about 4x more just a few years later. It might take some hard work but here are 7 actionable tips that can help you in the process.

Continuing The Story

At the point that I paused my earlier backstory, I self-taught myself technology, changed careers and moved to another state for a higher paying opportunity. At the end of that post I wrote:

“I had a couple more job changes within the same career field. Ultimately what I learned – in skills from self-training, and experience from the positions I held, and also from taking calculated risks – put me in a position to start my own business. But that’s a story for another day…”

Today’s that day.

While doing all of the studying and learning that I previously mentioned, I was also putting those skills to use. My area of exploration was technology, specifically with coding (creating programs). What I would do is take whatever I had learned most recently and implement it. It didn’t matter what the program did – it just needed to work as expected. This allowed me to fine-tune my knowledge. It also provided a LOT of real-life troubleshooting experience. Because, believe me, rarely did something work as expected after my first attempt.

The Side Hustle

While I was learning – and still working a full-time job – I took on some side projects. I was able to locate a couple of small businesses that either needed programming or web design. This was in the mid-90s so we didn’t have all the fancy tools that we do today. Even WordPress wouldn’t be released for another seven years.

Those first two years of side-hustling honestly weren’t quite break-even financially. After the courses, hosting, tools, internet access, and other needs were covered, there wasn’t any profit to speak of.

But I was gaining a ton of experience. With every project, I got better and more efficient. My client base also continued to expand.

The Pivot Background

Right around this time, the Internet was “becoming a thing”. Netscape (remember them?) was a fairly new solution that let people surf the web for the first time. Because of these advances, clients started asking for code that would run on a website.

Guess what? I had to teach myself Internet technologies to deal with this shift. It was hard work. Back then we couldn’t just “Google something” to get an answer. It was mainly trial and error. Emphasis on error. But I was able to figure most of it out and make the transition into web development.

It was exhausting because I was working nights and weekends while I still maintained my full-time job. Thankfully my wife is an amazingly understanding and supportive person. I couldn’t have made it work without her.

Two years after I had started writing desktop applications (for Windows) I found myself with a decent-sized group of clients with steady website work. In those early days of generally accessible Internet, it was hard to find decent web hosts. Clients constantly commented about poor levels of support everywhere they tried to find hosting.

Problem identified; solution developed.

The Pivot

So I bought a server, found somewhere to locate it with fast Internet access, and started hosting. The new venture was named ORCS Web, Inc. (aka OrcsWeb).

Two years into it, we were making money. But not much. Not as much as I was making in my full-time job. But it was bringing in close to what my wife was making.

So guess what she did? Just like I did a couple of years earlier, she put in the work to learn the business and the technology. If you know her, you know she isn’t a tech geek. This was hard work for her. But she saw the potential and she wanted it for us. She did what was necessary to make it work.

Staffing Up

And work it did. Over the years we went on to hire dozens of employees located across a half dozen states. We even had one employee in Canada for a while.

About five years after starting this venture as a side-hustle, Karla and I were comfortable enough with its size and steady growth that I was able to join full-time.

Yes. Two years to profitable. Five years to replace my salary and benefits.

If you are thinking about starting something – and I’m all for that – you need to think long term. Overnight successes are largely a myth. Most “overnight successes” take years to gain real traction. Do it. But understand the work and time required.

Funding The Venture

We never took angel or venture capital. I’m not 100% against it, but I’m a much bigger fan of bootstrapping.

Bootstrapping is building a business with your own money and the money from the business. It’s using the business to fund itself, even if that means slower growth than if someone invested in you.

The only outside money we took was from a small number of family members. These were people who likely didn’t understand what we were doing, but they believed in us. It was just a few thousand dollars – to buy that first server. They probably assumed they would never see the money again. So I’m sure they were happy years later when they got many times their original investment back.

Yes, they owned stock in the company. (What are stocks?) Just like if you bought shares of Apple in your investment account. We weren’t publicly traded, but it’s literally the same concept.

We also set up an Employee Stock Ownership Program (ESOP) and gave 20% of the company to the staff.

Other Benefits

Besides getting a salary and sharing in the profits of our company, there were a number of other benefits that were very important to us. Some of those additional benefits were:

  • Being able to work from home. Every one of our employees worked from a home office. No sitting in traffic commuting to and from work. Walk ten yards (or whatever) to your desk and you’re at work. This isn’t for everyone, and you need to structure it properly, but it can be great! It’s a very appreciated employee perk and saves a ton of money for the company.
  • Being able to work from anywhere. If we – or any of our employees – needed to travel for some reason, they had the option to still work. As long as the employee had their laptop, cell service, and reliable internet, they could work from almost anywhere.
  • Extreme flexibility. Don’t hear me wrong. Karla and I worked seven days a week and at least twelve-hour days for many, many years. But, we had flexibility with our schedules. We never missed our daughter’s swim meets. We all got to eat dinner together every night. The ability to shift, even if slightly, our schedule to accommodate personal priorities was important to us.

The Exit

Eighteen years after starting the business, we sold it.

The business was still growing, but slower. Our competitors over the last few years had names like Amazon EC2, Microsoft Azure, and Google Compute. The space was getting crowded and competitive. No matter how awesome you are, it can be hard to fight big brands’ marketing machines.

For about a dozen years we had regular inquiries from companies that wanted to purchase us. Until that final year, we really weren’t interested. Once we decided we would consider it, we looked around for an option to hit three priorities:

  1. Fair and reasonable value for the shareholders. We were nice people but we weren’t going to give the business away.
  2. Continued good treatment of clients. There was no way we’d sell to one of the large well-known chop-shops who would ignore the clients and just squeeze dollars from the business.
  3. Retention of the majority of staff. I knew as CEO & Founder that my position wouldn’t be part of a deal. Companies don’t need two CEOs. I also figured we’d lose a couple of people because of overlap. But I wanted most people to remain employed.

This was tricky but we finally found a match and closed the deal in July of 2014.

Financial Planning for Business Owners & Entrepreneurs

The Second Million

I’m not allowed to disclose details of the deal. I do want to share some thoughts though because many people haven’t considered certain aspects of a business sale.

Like many businesses, we had a variety of ownership. Remember we gave 20% of the company to employees. We also exchanged shares of stock to family for the original investment. Our remaining ownership stake was in the 50-something percent range.

A million-dollar sale can look a lot like $500k to the founder. Keep this in mind if you are starting a venture and thinking about bringing in investors. They’re likely investing for a big payoff, which means a small payoff for you.

Also, don’t forget taxes. Even though a business sale is considered long term capital gains (if you structured the deal properly), that’s a lot! 20%+ goes to pay federal taxes. State taxes can be up to another 13%! There’s a third of your profit gone in taxes. Even if you owned the full company and sold for a million dollars, it would look a lot like $650k after taxes. Ouch.


I love entrepreneurship. That includes doing my own thing and helping others. It’s exciting to build something that adds value to both the owner(s) and clients.

Frankly, I think most people should at least experiment with a side-hustle. Even something small like driving for a ridesharing service or affiliate marketing.

It puts you in control of your own destiny.

Yes, it is a lot of work. But it is work with a direct payoff for you. Employers pay you less than you add in value to the business. At least that’s the case if they are running their business well. When you work for yourself you get compensated directly in relation to the work and value you provide. There is tremendous potential in that model.

In Closing

Are you an entrepreneur? If not, have you thought about it? What’s holding you back? Let us know in the comments section below.