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Updated on July 29, 2022 11:42 pm
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Updated on July 29, 2022 11:42 pm
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Updated on July 29, 2022 11:42 pm Enters New Era – JLCollinsnh


Shawn and Jocelyn with Jane and JL in Steamboat Springs, CO 2021


In the beginning…

Forgive me if you have heard this tale before. I’ve told it several times now on various podcasts. It is the origin story of this blog.

Back in 2011 I began writing a series of letters to my then college age daughter about things financial. See, in the years before I had managed to turn her off to all such matters. 

Who knew a four-year-old wouldn’t be enthralled with the Wall Street Journal and the story of Jack Bogle and how he created Vanguard and index funds? But there you go.

Try as I might, she kept saying, “Barney’s on!” making it very much sound like she’d prefer to watch that. Who would have thought?

Anyway, because life is so much better, richer and free if you understand money and so much more difficult if you don’t, I very much wanted to be sure the information was around for her when she was ready. Even if I was not.

I shared some of these writings with a business pal of mine. 

He said, “This stuff is pretty interesting. You should put it on a blog and share it with your family, friends and associates.”

This struck me as a great way to archive the information and so was born.

Why the blog has such a boring name…

This also explains why the blog has such a pedestrian name: I wanted those family, friends and associates to know it was me.

They, of course, didn’t care. But, amazingly, other people around the world whom I had never met did, and the readership began to grow.

I should have come up with something cool for a name, like Go Curry Cracker, Mr. 1500 Days, Millennial Revolution, Afford Anything, Mr. Money Mustache, The Mad Fientist, Life Outside the Maze, The Humble Penny, Can I Retire Yet, or any of the countless others

But I didn’t and by the time it occurred to me that might have been a good idea, my boring jlcollinsnh had begun to garner some brand equity and it was too late.

Growth and problems…

Regardless of the shortcomings of the name, more and more people found it — and found it resonated with their FI needs and journeys.

At first, it was hosted on WordPress free of charge. But then at a certain level, this was no longer an option. With the help of some blogging friends, I moved it to a new platform. Now it started to cost me money.

At first, it was only a few hundred dollars a year and I didn’t care. But then it grew some more and a still newer, more robust platform suddenly was costing a few hundred dollars a month. And now I did care.

To offset these costs, and to satisfy the IRS who demanded at least some revenue if I was going to write these expenses off, I went to FinCon and began to learn how to monetize it.

Now, as readership continued to grow, along with expenses, so did the income to pay for it all. It even began to turn a small profit.

But as this growth accelerated, so too the complexity of the technological expertise needed to keep it up and running. Expertise I was, and am, notably lacking.

My more tech-savvy friends helped, but soon the issues outstripped their abilities and available time.

Along about 2014, to my horror, the blog began crashing. No sooner would we get it back up, than it would crash again.

There is only so much you can expect of your friends, and I had far exceeded that line. It began to feel like the Universe was telling me the time to shut it down and step away had come.

I was about to do just that…then Lucas appeared.

Lucas appears…

There is, of course, a perfectly ordinary story about how Lucas appeared. But I have chosen to forget it. I remember it as magic, an act of the gods.

There, moments before I hit the auto destruct button, his email manifested itself in my inbox.

“Hey,” it said, “I really like your stuff and think it is very important to have out there. If you ever need any tech support, I’d be honored to handle it. Free, of course.” Or something like that.

We Skyped. He seemed to know his stuff, but what do I know? He seemed reliable, but what do I know? He seemed sincere, but what do I know? He seemed to be the answer to my prayers, but what do I know?

What I did know was that I would have to give him complete access to the blog for him to work his magic. That seemed like an enormous risk. Once inside, there was no end to the mischief he could cause were he so inclined. And, he was just this guy in Tennessee I didn’t really know at all.

I turned to my pal, Mr. Money Mustache, for some guidance. 

“JL,” he said, “you have got to be more trusting. Most people are good and genuine.”

“Well, maybe…”

“Plus, you’re about to shut it down anyway.”

Well, yeah, there was that.

I turned over the keys to the kingdom and held my breath.

Lucas takes over…

Keys in hand, he entered the kingdom, waved his magic wand and all the problems disappeared. 

He says there is no magic wand and that it was a simple matter of correcting some easy tech issues.

But ever since, anytime there has been a tech problem, I make Lucas aware of it and it magically disappears. 

I’m pretty sure there is a magic wand in there somewhere.

True to his word, through the years he has continued to refuse payment. But this bothered me. So every now and again, I send him a bunch of money.

He always replies, “You don’t need to pay me. I’m not doing this for the money.”

And I always reply, “I’m not paying you. I just found this money lying around and didn’t know what else to do with it.”

The years roll on…

The blog continues to grow, it is nicely profitable and it operates smoothly. My daughter has even taken an interest and, with some arm twisting, begins helping with the affiliates. Revenue grows.

But she is not really interested and, not to put too fine a point on it, I am getting old. My thoughts turn to how to keep the blog and its content up and available long into the future.

The only thing I can think of, is to sell it — hopefully into strong hands that will respect and maintain the work.

Up for sale…

Working with my pal, JMoney, we prepare an offering document and put it out to his select list of potential buyers. It draws immediate interest.

Soon we are down to four prospects and things are getting serious. Documents are being drawn up. I decide it might be a good idea to get some outside perspective. 

I email my pal, Shawn.


I met Shawn when he and his wife, Jocelyn, came to Chautauqua 2018 Greece. We hit it off immediately. They returned for Chautauqua 2019 Portugal as friends.

Jocelyn and Shawn meeting JL at dinner in Greece 2018

Shawn is one of the most accomplished business-people I know. He started a tech company from scratch, grew it, took it public and then ran it as CEO for several years. 

When he decided to step away, he turned his attention to building a children’s hospital in his town of Charleston, SC. That done, he kicked back for a couple of years.

He looked over the documents I had sent him, made a few observations and said with those few changes they looked good. 

Then he surprised the hell out of me.

Shawn’s surprise…

“You seem to have reservations about letting the blog go,” he said.

“I do,” I said, “but I think the time has come.”

“It sounds like you want to offload all the hard stuff and just keep doing the fun part of posting. At least on the rare occasions these days that you actually post.”

He laughed, and so did I.

“That about sums it up,” I said.

“So why don’t we do it together?”

I was stunned.

“That certainly works for me, but I’m having trouble seeing what is in it for you.”

“I’m a huge fan of your work, we have fun hanging out together, and I want to be the one who makes sure it lives on for years to come.” 

We kicked ideas around for a couple of months and, on Dec 7, 2021, we inked a deal.

What the future holds… will remain my blog, in content and ethic. However, it now has a team behind it and it will continue far into the future and long after I am unable to work on it.

That team will include Lucas, who will be on retainer and will finally be getting officially paid. I confess, I am a bit surprised he has agreed to come along. When I first told him I might sell, he was clear that would be the end of his participation.

But he likes this new plan, this team, and the cool things it will bring. Namely, those things he and I have long wanted to do, but for which we had neither the time nor — in my case — the energy.

We both also like the ideas Shawn and his team have suggested.

To be clear, none of this will happen immediately or all at once. But it is definitely coming and the prospect has renewed my enthusiasm for the blog and its future.

Stay tuned!

A note from Shawn…

Thank you for the kind words, JL, and thank you for allowing me to partner with you on your blog. 

Hello to the community! I have been a fan of the blog and JL’s book for many years. JL and I talk often, and we’ll share a link to an interesting story or blog post when inspiration hits. So when I received an email from him several months ago, I was eager to see what nugget he had for me. I was surprised to read that he had been considering selling his blog and had gone so far as to have a list of finalists. 

We exchanged a few emails on the subject, and he asked for my input on a framework for the offers he had received. We had a few video calls and discussed the possible transaction, and I kept digging at why he wanted to sell and why now. It became clear to me that he didn’t want to step away from his blog and the community, but rather he was looking to offload the administrative burden and turn some of the value built up by the blog into what I would call an estate planning strategy. 

As I studied the offers and the possible structure of the transaction, I kept thinking to myself, His blog is worth more than this. He actually had what most would consider very good offers and very flexible terms. However, knowing JL and his community, I could easily see lots of upside if JL would continue to write and the FI community would continue to grow.

Now, I wasn’t in the market for a blog. I’ll share a bit more of my story below, but suffice it to say, I really enjoy a clear schedule with very little in the way of formal work. But I knew the blog should be worth a good bit more than I was seeing in the offers, so I expressed my interest in purchasing it. 

That statement led to a series of conversations with my wife, with JL, and with a few folks that I work with on several business initiatives, including my oldest son, Alex. After discussing the idea with my wife for a few days, I asked her one evening, “So should we create some sort of deal to be in the blog with JL?” Her answer was immediate and resounding, “Yes! We love JL and Jane, we are big fans of his book and blog, we have five kids and we share his writing with our kids in the same way that he began the blog to share with his daughter, so sure, we should absolutely be part of the future of the blog with him!”

Many iterations of agreements later, here I am introducing myself to you. 

One last thing on our involvement with the blog, the main condition I had on the “deal” with JL was that he had to remain the face, voice, inspiration for the blog. I had no problem with the price or taking on the administrative work and pulling a team together to help with the blog’s next phase of growth, but I would not jump in unless it continued to be JL’s blog. 

I also spoke to Lucas about his interest in remaining with the blog. Thankfully, he was interested and agreed to join the expanded team. So we worked all that out, and JL will continue to write and do interviews but without the burden of the administration. My motivation was and is primarily to steward JL’s work well into the future.

Now that you know how I got here and why I wanted to be here, here’s a brief version of my story…

I’m a husband and father of five. We are a tight knit family and spend loads of time together. 

I grew up in a single mom home near Daytona Beach, FL. We worried about money a lot. I started working at age twelve and had over twenty different jobs prior to eventually starting my own company. 

After many jobs in many different industries, I found my way into the software and internet field and started a company called Benefitfocus with a friend in 2000 (three months after the dot-com crash). I served as the CEO from startup through an initial public offering (IPO) in 2013 and on to over $250m in annual revenue in 2018 and a valuation of over $1b. I loved the entire journey. Then in 2018 I decided to step away and take some rest. 

You can follow my journey on my blog

The personal fear of running out of money drove me well past the level where our company was successful, and on paper I didn’t need to worry any longer. It took me years to unlearn some of the patterns I had in my mind. So when I discovered the financial independence (FI) community while still serving as CEO, I really soaked up the stories of simplifying your life, simplifying your investment strategy, and designing a more flexible and relaxed lifestyle. I even began to teach some FI courses at my company, encouraging people to design their best life and use our company as a platform to achieve financial independence.

The first few FI blogs I found were JL’s blog, Mr. Money Mustache, Financial Samurai, Frugalwoods, and the Mad Fientist’s podcast as well as the ChooseFI podcast

After the Chautauqua in Greece where I met Brad and Jonathan from ChooseFI, I joined them as a board member in their newly created ChooseFI International Foundation

I also recently started another software company with two longtime friends and co-workers. It’s called 3Together. We have a unique culture and at our first company get together we had JL call in via video and answer questions. We also purchased The Simple Path to Wealth for each member of our team and openly encourage everyone to work toward their own version of financial independence and use the company to accomplish their personal goals. 

So thanks again, JL, for allowing me to join you in the future of the blog. I am sure we will have a lot of fun, and with the help of our expanded team, we will create even more great content for the community!


Chautauqua is back!

On February 10th, I’ll be posting about Chautauqua 2022: Colombia! 

As will each of the other speakers. We will be doing two weeks back-to-back in September and, as always, there will only be 30 attendees at each week. This small group dynamic is part of the magic.

So, if you want to come be sure you are on the mailing list here:

February 10th is also the day tickets go on sale. With only 60 slots, you’ll need to be quick. No joke.

Hope to see you there!


Source Enters New Era – JLCollinsnh is written by lucas for


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