How We Made Our Second Million

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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 post Here’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 our 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 into 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 who 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.


By the way, the host we use for this site – and highly recommend – is SiteGround. We tried a few other hosts and they didn’t hold up to our quality standards. SiteGround is top-notch in both performance and their support staff. They have WordPress hosting starting at just $3.95 month. If you want a quality host, check them out.


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 it’s size and steady growth that I was able to join full-time.

Yes. Two years to profitable. Five years to replacing 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.

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.

Entrepreneurship

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 with Uber 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 thats 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.

 

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15 Comments

  1. Tom @ Dividends Diversify October 3, 2017 at 5:05 pm - Reply

    I’m not an entrepreneur, but admire those who are. Congratulations on your success. I’m sure it took a lot of hard work and determination. Tom

    • Brad Kingsley October 3, 2017 at 6:52 pm - Reply

      Thanks Tom! I think the entrepreneurship was subconsciously instilled upon me by my father. I think I’ll write a post in the future on how he modeled that while my brother and I were growing up. I appreciate the comment and kudo!

  2. Bernz JP October 3, 2017 at 6:49 pm - Reply

    Thank you so much for this encouraging article. One of the obstacles in getting the business to the next level is finding a good or simply finding a partner who you can share your vision to. I’ve developed an online business targeting the Japanese market last year (after two years in development). I guess I did not do an intelligent homework on this one and never thought that I will need a Japanese partner to prosper in this business.

    Hopeful still.

    • Brad Kingsley October 3, 2017 at 6:53 pm - Reply

      Thanks for reading Bernz! Yeah, launching a venture targeting a foreign market is tricky for sure. It would definitely help having a partner who was well-versed in the customs and practices of that demographic. I hope you find the perfect partner to make this is big success!

  3. Laurie Blank October 5, 2017 at 10:13 am - Reply

    Thanks so much for sharing your story, Brad. I am finding similar results (on a much, much smaller scale 🙂 ) with the recent sale of TFF. When I tell ppl how much I sold it for, they’re like “What???” It doesn’t make sense to them that I sold an online site for so much money. Entrepreneurship can be a great way to go for many people!!

    • Brad Kingsley October 5, 2017 at 7:31 pm - Reply

      Thanks for sharing Laurie – and congrats again on the sale of TFF! Yeah, people are surprised. It makes sense though. Something that brings in steady, fairly predictable, revenue are worth $$$. It’s a better model than where you have to sell to a new client over and over each month. These recurring revenue models are the way to go for sure! Thanks again for commenting!

  4. GYM October 14, 2017 at 3:26 am - Reply

    Wow amazing story! Thanks for sharing. I also sold my blog a few years ago (in 2012 after starting it in 2009) and now I’m starting another one again in 2017 (but different name). It was a great feeling to sell, even if it was just for five figures (not a million bucks like you! lol).

    • Brad Kingsley October 14, 2017 at 11:18 am - Reply

      Thanks Gym for stopping by and commenting. That’s awesome that you’ve sold a blog and are now building another one. Hopefully this new one will be even more of a financial benefit for you – in addition to all the other benefits of doing your own thing.

  5. Mrs. Adventure Rich October 16, 2017 at 7:41 pm - Reply

    We are still working on our FIRST million, but I like the idea of looking to and planning for the next million 🙂 We are not entrepreneurs at this time, but certainly are not counting this out for the future!

    • Brad Kingsley October 16, 2017 at 7:44 pm - Reply

      Mrs. AR – thanks for stopping by and commenting! I’d say you ARE entrepreneurs already. You have a great blog over there! If you aren’t already making money with it, I’m sure you will. Just keeping being awesome. 🙂

  6. Working Optional October 17, 2017 at 2:19 am - Reply

    Wow – YOU’re the guy (team) behind Orcs Web? I think I recommend you’ll to a few clients back in the day. Thanks for providing great service.

    Your post hit home on more than one front. Instead of focusing on what isn’t right, one should focus on what they CAN do/change about their situation. Great post, as always.

    • Brad Kingsley October 17, 2017 at 12:01 pm - Reply

      Hey – that’s cool that you’re familiar with OrcsWeb! Referrals were always appreciated – it’s the #1 source we had for new clients.

      Thanks for reading, and for sharing those thoughts!

  7. Physician on FIRE October 17, 2017 at 4:01 pm - Reply

    Good for you, Brad. I’m impressed your business was in the same space as some serious heavyweights — and congrats on that payday. I certainly remember Netscape. Also Mosaic.

    The tax issue with selling a business is a big one. Just like collecting dividends or capital gains from the sale of stocks or funds, state income tax can be painful. With a million dollar sale, you’re automatically in the top federal income tax bracket, which gives you the 3.8% ACA surtax (NIIT) plus the extra 5%. With a multimillion dollar sale, it could be worth considering moving to a low-tax state for a year. Hypothetically, selling a business for $5 million as a resident of California versus Nevada will cost you an extra $665,000.

    Cheers!
    -PoF

    • Brad Kingsley October 17, 2017 at 7:23 pm - Reply

      Thanks PoF! Yeah, the space got pretty crazy with heavyweights – we got out at a good time for sure.

      Yeah, the tax issue is HUGE – for the reasons you mentioned. It is possible to literally lose half of a million dollar sale once all the taxes are calculated.

  8. Jason@WinningPersonalFinance November 9, 2017 at 12:49 am - Reply

    Congratulations on building and selling a successful business! Not many people can say that. I never considered the impact of state taxes on the sale of a business. I’ve been thinking a lot about geo-arbitrage lately and this is just another reason why it might make sense.

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