I love hearing the unique stories about how multiple people reached financial independence or retired early (FIRE).
Sure, the Internet is great for cat videos and political rants on Facebook. But for some people, it’s also a giant money-making machine. I tracked down two of those people, from drastically different walks of life and industries, and asked them to share their stories.
These aren’t “get rich quick” stories; these are everyday people with full-time jobs who decided to start some online work on the side.
Rob Berger, DoughRoller.net
Rob retired from practicing law two years ago at 49, based on income from his personal finance blog DoughRoller.net. Earlier this year, he retired from blogging too, after selling the blog for an undisclosed — but presumably large — sum.
Getting started
Rewind to 2007, when Rob was 40. “I was bored practicing law. My wife told me to get a hobby. At first, I planned to be a woodworker, but one day I came across a personal finance blog. I love technology, and I love personal finance investing. It was a marriage made in heaven.”
When you find a hobby that earns you money, rather than costing you money, you’re onto something. He immediately decided to launch his own personal finance blog.
Growing the Business
Rob goes on to explain that the early days were slow.
“At first I was doing 100% of the work. Over time, I met other bloggers and others in the media field. For example, about eight months into blogging, I developed a relationship with MSN money. They syndicated some of my content, and that’s when the site started to take off.
“As time went by and revenue increased, I started to hire contractors to help me. This allowed me to offload some of the writing and technical details of running the site.
“One game changer was the launch of my podcast in 2013. While the podcast didn’t generate any revenue, it did help me build a very enthusiastic following. And it’s something that I’ve continued doing even after the sale of my sites.”
“The turning point was 2010. That year I realized I could make as much or more blogging as I could practicing law; that being said, I didn’t fully retire until 2016. I’m a slow learner.”
What Early Retirement Required of Rob
What does it take to succeed as an online entrepreneur?
“Without religious-like dedication to building a blog, you’ll never succeed. When I started, I got up seven days a week at 5 a.m. On workdays, I would work for two hours and then get ready for my day job. I would work on my blog on the subway going to work, virtually every day at lunch, and in the evenings after my family went to bed.”
Even after several years of relentless work, Rob barely eased off the throttle.Still, as more revenue started streaming in, that gradually changed. “By the time I sold the site earlier this year, I had contractors helping me with revenue, editing, and social media.”
For Rob, to be successful, “You have to be willing to learn a lot; ask the right questions. In short, just be curious. Curiosity combined with grit can accomplish just about anything.”
Zach Hendrix, GreenPal
Zach’s online business, GreenPal, has been described as “Uber for lawn care.”
Here’s how quickly your life can change, as an entrepreneur: “When we launched our business two years ago we had no money and no outside capital to get started with. This year we’re going to surpass $10 million in annual revenue.”
As fast as Zach has grown GreenPal, much of his success revolved around being forced to wait and refine his business model.
Getting Started
Zach’s story begins all the way back in high school, and how his father helped lay the mental foundations for success. “When I was in high school I was very fortunate that my father gave me a classic book from the 1930s, The Richest Man in Babylon. When you’re forced to pay yourself first each month it forces you to live within your means.
“The author talks about how if you desire to purchase something, you must first acquire the asset that will deliver the return needed to purchase whatever it is.”
This mentality helped Zach become a professional property manager and landlord, with ten rental properties of his own. This, in turn, helped him notice an unmet market need. “We saw how hard it was to order lawn mowing services. It’s a real pain just to get somebody lined up for a regular grass cutting service and keep them showing up on time.
“On the flip side, for small lawn care professionals, it’s very difficult to find good-fit clientele, and maintain a well-organized business, especially if nobody has taught you.”
Zach and his partner had a good idea. But how to go from idea to reality?
From Slow to Go
Zach’s original idea was far broader, without this niche focus. “Like most tech startups we went on the fundraising circuit talking to angel investors and venture capitalists begging for money to get started. However, our vision was just too broad in scope and luckily we got turned down and told ‘no’ over 40 times.”
Only in hindsight do entrepreneurs relish hearing “no.” But Zach and his partner went back to the drawing board and niched down their contractor-client connection platform idea to focus specifically on lawn care.
And they realized they didn’t need massive venture capital funding. “I was fortunate enough to have solid personal credit; this enabled my team to secure an unsecured line of credit for $85,000 to get our business started.”
Within the first year, they paid off that line of credit in full.
From Here to Eternity
For Zach, the rejections were a blessing in disguise.
“Good thing early investors told us ‘no,’ because with their capital they would have owned and controlled 30% of our business. Because we’re self-funded, my cofounders and I own it all.”
Today, Zach still owns and manages his own rental properties. But he no longer works 9-5 as a property manager. “My passion is growing this company to a nationwide network of tens of thousands of lawn care service providers completing hundreds of thousands of transactions a day.”
Could Zach sell his company and retire? Sure. But when you find a project you’re passionate about, why would you want to give it up?
Final Thoughts
So, what does it take to become a successful online entrepreneur? Here’s a hint: the answer doesn’t involve massive startup capital. Neither Rob or Zach spent much, relatively speaking, to build their businesses — but they both worked incredibly hard.
Each experienced massive setbacks, and days that looked hopeless. It’s inevitable. But one of the core differences between successful entrepreneurs and flops is standing back up, dusting yourself off, and saying “Well, we know that didn’t work. What else can we try?”
Calculated risk is another theme: Zach took on debt to launch a project he believed in.
And in return? Both digital entrepreneurs sit in their own driver’s seat. Rob already retired and could have retired years earlier; Zach has chosen to keep working, because he loves what he does.
Here’s a final quote that another entrepreneur shared with me: “Money can be earned again. Time lost can’t be regained. So, my core idea is to protect my time at all costs.”
That’s the beauty of financial independence — you suddenly have complete control over how you spend your time.
Photo Credit: Michael Cory
Thanks for this. Good article.
Glad to hear you enjoyed it Sam!
Loved the story of these 2 entrepreneurs. Blogging is much more competitive now, but hard and smart work coupled with perseverance can still pay massive dividends.