Today I am featuring Steve Miller who reached Early Retirement at the age of 50 after selling his multi-million dollar software company. It’s the amazing story of a journey to FI/RE, about the power of long term goals and what actually happens in Early Retirement.

As a bonus, Steve also shares some cool pieces of wisdom throughout the article and advices for aspiring entrepreneurs.

I hope you find it as inspiring as I did. Enjoy!

Steve, tell us about you and your story

My name is Steve Miller and I retired early, at the age of 50. I graduated college in 1984 and worked for Ross Perot’s technology company as a software engineer. After working for Ross for 10 years, I branched out as an independent consultant and my first project was working at Microsoft in Seattle. I later moved my consulting practice to Denver to enjoy better weather.

My primary job as a consultant was to rescue failing projects that had spiraled out of control due to mismanagement. I discovered that with process and tools, these projects could be fixed in short order. But there were barriers. Tools were expensive and to do the job, you needed several tools (project management, defect tracking and test management). Necessity is the mother of invention.

Necessity is the mother of invention.

After helping rescue several software projects, I convinced my wife to let me start a company. She was nervous because I was making great money and it required living on our savings for 6 months while I developed the product. It was a bold move, but I knew I could always return to consulting if it didn’t work out.

My product addressed 2 major problems I saw in the industry. Clients needed an integrated tool and they needed it to be affordable. So in 1999, I developed the first version of the product and allowed companies to rent rather than buy it. That reduced their costs and allowed me a predictable monthly revenue stream by billing them on a monthly basis. It was a win-win.

Fast forward 10 years later. I built that idea into a multi-million dollar company and received a call from a venture capital firm from NY asking “Would you ever consider selling your company?” Yes sir, I would!

Getting in business

Once I convinced my wife to let me start the company, I wrote a business plan. In the business plan, I clearly stated “I would like to sell this company and retire by the time our kids go off to college (that would be 14 years in the future, in 2013)”.

Always start a business with the end in mind

I also stated in my plan how I might accomplish that. I would seek out larger companies that had complimentary products and try to partner with them for a combined solution. At first, there were lots of companies that fit the bill but I did not have enough market share to attract them. So over the years, I grew my market share and built integrations that made our product work nicely with a few others.

The company that was backed by the NY venture firm was one of the products I had spent about a year partnering with and we began selling each other’s products successfully and mutually benefiting from it.

Always start a business with the end in mind.

What’s one of the toughest challenges you faced in your business?

Our first customer came the first month we were in production. I designed it as a web application which was pretty unique at the time. The rent vs. buy feature also made it very attractive for small to mid-sized companies. I focused my marketing on internet sales using search engine optimization (SEO) and later using Google Adwords as my primary lead generator.

the World Trade Center disaster happened on 9/11/2001. Businesses went into Lockdown mode

The software started gaining traction between 1999 and 2001, then the World Trade Center disaster happened on 9/11/2001. Businesses went into lockdown mode and the tech bubble burst. We saw sales decline and the software was no longer selling itself.

To remedy this, I hired a full-time salesperson and began providing online demonstrations. After prospects downloaded our software, the salesperson would cold call them convincing them to sit in on an online demonstration of the product that I conducted daily. This approached worked so well that I eventually hired several full-time salespeople to scale the operation. As our market share started to grow, our software won several awards. This made it easier to partner with larger companies and eventually we built integrations with several companies, solidifying my initial plan to sell the company to a larger company we partnered with.

What has been the greatest satisfaction of this journey?

The greatest satisfaction was selling the company before I had planned. In my original business plan, I wanted to sell the company by 2013, when my two sons left for college. Even with the recession of 2009, we found a way to sell our company earlier than planned. This gave me breathing room to transition the company over to the acquiring company while my kids were finishing high school.

Why did you sell?

Selling was a no-brainer, I had planned that from the beginning. When the call came, I did not flinch. The biggest issue I struggled with was that structure of the deal. When you sell a company, normally it is structured with an upfront payment, a couple of earn outs, and possibly some stock.

The initial proposal was to receive 1/3 of the agreed upon price up front, 1/3 after year 1 (if we hit specific revenue targets) and 1/3 after year 2 (if we hit another set of revenue targets). I renegotiated that to provide ½ up front, ¼ after year 1, ¼ after year 2 and stock in the acquiring company. I also agreed to be hired as an employee (VP of my division) to ensure that we achieved the revenue targets for the earn-out. By doing this, I focused our team on hitting our targets and we crushed the earn-out revenue targets.

After we achieved our earn-outs, I tendered my resignation and officially retired. This aligned perfectly with our kids graduating high school and my wife and I were free to travel and experience our second phase of life.

Entering Early Retirement

After I retired, my wife and I did something we always wanted to do: we traveled. Literally the month after we retired, we saw our boys off to college and began traveling. Starting in Canada, we visited the maritime provinces of New Brunswick, Nova Scotia and Prince Edwards Island.

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We then made our way to the Galapagos Islands, Machu Picchu and the Bahamas. We saw extraordinary things. We watched a tortoise painstakingly dig a hole for her eggs.

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We saw the handiwork of the Incas, appreciating the architecture and incredible surroundings of a civilization that’s now long gone.

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The next summer we spent traveling around the western US, visiting the Grand Tetons and Yellowstone. We saw the huge redwood forests of California, stayed in an old farm house steps away from the shores of Canon Beach, Oregon. Then we made our way up to Seattle to enjoy the weeks leading up to the fourth of July. From there we headed to Vancouver, Canada for 3 weeks, cycling around Stanley Park and hiking Grouse Mountain. We ended that trip with a 2 week cruise to Alaska, watching the glaciers break apart and fall into the ocean at Glacier Bay.

Last summer, we took our youngest son to Europe. We planned the trip around the Running of the Bulls in Pamplona but spent time in Paris, Spain, Italy and Portugal. The Running of the Bulls is something everyone should experience. It’s festive, raw and invigorating. The Italian Riviera is a sight to behold. Beautiful oceans held in by massive cliffs and quaint seaside villages.

Italy-Nice location for Early Retirement

Relying on the 4% Safe Withdrawal Rate (SWR)

Our plan is to keep our spending between 3% and 4%, but in our early years we have been spending more along the lines of 5%. This is due to having 2 boys in college and traveling extensively. Luckily, in the 6 years since we sold our business and became financially independent, our portfolio has grown even at that spending level.

By retiring early, I’ve had a chance to assess what I really love and I’ve boiled it down to 3 things that get me excited: lifestyle freedom, financial independence and technology. I love to write, so I started a blog called We Retired Early where I focus on those things.

To align our spending level between 3% and 4%, I am monetizing my blog and writing mobile apps that generate passive income. Right now, I have an app in the app store (aMemoryJog Password Manager) and another coming out later this year (Count Us Down App).

I’ve designed this new business as a lifestyle business. Because I am not dependent on a paycheck, I can work as little or as much as I desire and we can continue our travels. I normally work on the new business a few hours a day and spend a good portion of my day doing fun activities. I love to golf, hang out at the beach, go boating, cycle, workout and hike – this lifestyle business allows me to do those things. Some days I work as much as 6 hours, some days I don’t work at all.

Any advice for our readers?

Reaching FIRE can be done one of two ways: greatly reduced spending or by generating additional cash. I am not a big spender but I am also not overly frugal, so generating additional passive income is much easier for me to support our lifestyle.

If you are considering going down the route of starting a business, I would offer this advice:

  1. Do your research up front and build a good business plan. If you visit my blog (, check out the App Development section of the site. I discuss how to build a business plan and offer step-by-step guidance in building a business.
  2. Don’t quit your day job. When I started my first business, I continued to consult part-time, allowing me to supplement our income as I was building our product. Once our product replaced the revenue I was earning in consulting, I stopped consulting. But you really have to hustle and put the effort in, it certainly is not easy.
  3. To build a business, you need to self-promote, otherwise your message will get lost in the crowd. Having your own blog can help promote your offerings but you need to generate traffic to your blog. This can be done by building twitter followers and posting on multiple sites (I post on my blog, Medium, Stumble Upon, BlogSpot, Tumblr, and Pinterest). If you are really interested in this, sign up for my newsletter because I cover these and other topics in detail.

This is such an inspiring story Steve, thanks for taking the time to share it and all the best for your lifestyle business! 

Feel free to ask Steve all sorts of questions in the comment section and be sure to check out his blog at or follow him on Twitter, Facebook and LinkedIn.

How does Steve’s story inspire you? Who’s the next millionaire? 🙂

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  1. Great story and some fantastic life lessons. I’m curious how you discovered what you loved to do after your sale, I know that transition can be difficult sometimes (and it’s not like many people can relate to finding purpose after selling your company). Thanks!

    • Hi Jim — We first took time to travel because we always wanted to do that. In our first year, I think we traveled about 8 months out of the 12. Once we came back from our travels, I got a little restless and started looking for something to keep my mind active when it is wet and cold outside and I can’t get out and play.

      So I started developing mobile apps and blogging (check out my apps at

      I have always loved blogging. Last week I was approached by a company that wants me to help market their blog and I plan to do that a couple of hours a day, it is a great side hustle that will bring in about $3,000 a month for a couple hours of work per day.

      Thanks for stopping by!

  2. This is a great story Steve! It is great that you had an end game in mind (trying to sell by 2013). A lot of times you run into people who never think about what the end game is going to be for their company when they start it. The best part is you were able to complete your transition to FI before you anticipated end date!

    • Hi Thias! It really did work out well and I am well aware that things don’t always swing that way.

      We really hustled a lot, worked a lot of hours, and were focused on making it happen. When we sold the business, my wife and I looked at each other in amazement: we couldn’t believe we pulled it off!

      Thanks for stopping by!

  3. This is really inspiring! You guys did it right – hitting the road as soon as you could. I’m jealous! Wish you the best in your future endeavors. I like how you keep making new goals so you never stagnate or get bored . . . seems like you always have something going for you, but you are able to do the things you love now because you put in the work before.


  4. Inspiring to read, thanks to Steve for sharing. Gutsy I think to ‘check out’ with college tuitions still on the board, but seems to be working out well for Steve. Very smart I think, both financially and with respect to happiness, to start the blog and app business. Best wishes!

  5. Hi Steve!

    This is a great story. I started my blog early this year as a way to tell my story and help a few other readers (a few of my friends and my mom when I started out!). However, I’m beginning to see how passion, mixed with some hard work, and then a little opportunity, has the potential to not only change the lives of a few of the readers, but also mine as well. I’m curious Steve, did you always know it was going to work? Especially after 9/11?

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