Justin Ferriman

Justin Ferriman

This week Lorena and I arrived in Mexico to visit family, and to attend the presentation of our nephew, Diego, in the Catholic Church. In the ceremony, we were also confirmed as Diego’s Godparents. I am incredibly honored that my sister-in-law asked us to take on this role.

After the ceremony, there was a celebration with Lorena’s family (and let me just say, she has a huge family). I met family members that I have yet to meet, so I really enjoyed that. This also gave me an opportunity to further practice my Spanish. I must say that Spanish is coming along decently. The language is slowing down for me at times, making communication less stressful. I still have a long way to go, though.

We’ll be staying here in Mexico for an extended amount of time. In not so pleasant news, Lorena’s aunt Mica passed away after a hard fight with cancer. I had the opportunity to meet her last year when we visited Chicago for Christmas. We are awaiting word on when her ceremony will be back here in Mexico. She was a beautiful person, and even though I only met her once, I will miss her.

The trip is full of plans with friends and family, and also we will be going to Cancun for our one-year anniversary. I can’t believe it has already been a year, and what a year it has been!


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Well, it finally happened. The news in this country has pushed me to purchase a security system. These companies are selling piece of mind, and I’m buying!

Over the past month or so, I have been poking around with security systems. This is a really cool industry with numerous major players. Just as many review sites and YouTubers as well! You can quickly go down a rabbit hole trying to determine what is “best” for you.

For me, “the best” means having some cameras in place to detect activity inside and outside the home. I thought for a while that it would make sense to have an alarm system as well, but that feels a little unnecessary with the cameras. I also saw that some studies have shown that anyone who wants to break into your place isn't really concerned about alarms.

In any event, I decided to go with just some cameras. There are about a dozen recommended brands on the market – each with extensive reviews and opinions in Reddit. Of course, in my typical fashion, I ended up going with one of the brands that isn’t nearly as popular as the top five. 😆

Sticking with my newfound paranoia, I’m not going to share the brand of camera I purchased. Because you know… bad guys!

While I was on this shopping spree, I also decided to purchase a mesh router. I didn’t even know what this was until doing research on cameras. I guess it’ll help the signal of your internet (including to your cameras).

So, here’s to both getting safer and getting rid of those pesky internet dead zones!


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If you are like most people, then at some point in your life you have considered owning real estate.

Even people who don’t consider themselves to be entrepreneurs find real estate an attractive concept because it’s an easy business model to wrap your head around. Own a couple of low-maintenance residential rentals and let that other person pay off the mortgage while building equity.

Sounds great on paper, but as anyone who does this will tell you, things don’t always run smoothly.

I just need to look to my parents. During the recession of 2008, they purchase a few foreclosed condos. They are in a nice area with low crime and good schools. Even still, there is constantly something to be taken care of. Like the time their renter was literally stabbed by their crazy ass ex-husband, and was late on the rent by a few months because of the whole ordeal. I mean, there isn’t a book that can teach you how to deal with that.

When you peel back the onion, the reality is that real estate is not for the faint of heart. While it’s a great way to build wealth, it is not passive by any means. Depending on your property and the person renting, you may end up sinking insane amounts of time and money into the property to the point where you barely break-even.

I want to build wealth in real estate, but I prefer not to deal with the bullsh*t of having renters.

Upgrading appliances, fixing sinks, evicting squatters… I don’t have time for this. Okay, scratch that. I have time, but I want to spend my time dealing with it.

Still, the idea of real estate is very appealing to me, especially as I am completely burnt out from anything to do with the software industry, especially WordPress. As someone who started and sold a software business, there is something therapeutic about owning physical real estate. Like, you can touch it. It’s real. You can actually see the asset. Most importantly, it’s proven as the world’s oldest way to generate wealth – be it for a side income or a financial empire.

So, for me, it’s land > rental properties.

That’s not to say it’s all rainbows and butterflies. Land has its ups and downs, like any industry. But what I find refreshing is that the business model is straight-forward, with less complexity than other profitable industries.

Also, land is less impacted by the housing market. It is a little as you can imagine, but seeing as banks don’t generally provide loans for land in the first place, it creates additional opportunity for seller financing of deals (which has an added benefit of spacing out capital gains tax on a short-term flip).

I have already got the wheels in motion for this journey. I started off by getting the legal entities set-up and the business presence. All the software I am going to use initially has been configured and is ready to go. I’m also taking courses and getting up-to-speed with the basics because I don’t have a background in this business. Though honestly, that’s never stopped me in the past.

If I know anything about my learning style, I am a “ready-fire-aim” kind of guy. Give me the basics, and let me start working it. I know that I’ll make mistakes along the way, but I don’t sweat those as I know it’s a learning opportunity (I made a crap-ton of mistakes when running a software company, and everything worked out just fine).

Want to learn how to make money from land investing?

If you find the concept of land investing interesting, and you don’t want to worry about renters or fixing sinks, then I encourage you to follow along as I share what I learn!

I won’t be writing about it here too much, as this is my personal site and I use it to write about a variety of topics.

I started a newsletter where I document my journey in building a land investment business from scratch – with no prior experience. Think of it as my online journal of lessons learned, from “hell yes” to “oh sh*t”, and everything in between. Things like…

  • The strategies I use to find deals
  • Business set-up & tools
  • Marketing strategies
  • Growing a team
  • Automation of tasks
  • Making money buying & selling land

I hope you follow along with me, I promise you will learn something along the way!


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Today Lorena and I are flying to California, and earlier this week we learned that the mask mandate was lifted for airliners. All the airlines now have an optional mask policy.

This was discouraging news to us because honestly, flying has been one of the least stressful things to do in the pandemic up to now. Everyone was just rockin’ their masks.

It’s not the plane that I’m all that concerned with as the air filtration is pretty solid, it’s the airport and the boarding process. Airports are incubators of illness.

When I think back to the pre-pandemic days, I feel like there was a 40% chance I would get sick after flying, especially around the holidays. Everyone is just sitting around coughing and sneezing, multiplied by thousands. I’m not saying I think we need a mask mandate for public places, but yes for public transit. That seems like an insanely obvious choice. At least until we progress more combating COVID.

In any event, we continue to wear our masks. I won’t be mad at someone if they don’t have a mask on, they are just doing what they are permitted to do and to each their own. I’m just annoyed that this happened right before our trip.

And well, chances are that mask mandate will come back by the end of the year given the usual spike of cases.


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Lorena and I just got back from a trip to see family in both Connecticut and Michigan. As has become custom in the pandemic era, we were gone for an extended amount of time. This has its pros and cons (more pros, of course). It also means that we really look forward to our return home once the trip comes to an end.

But this trip home will be short-lived.

Soon we head out to California, followed by Mexico, which means that we will probably be back in Austin in early June. Similar to the most recent travel, these are family oriented trips.

The time in Mexico will kick off with the presentation of our nephew to the church (we are to be his Godparents). We will also try to plan a trip somewhere while in Mexico to celebrate our one-year anniversary!

Even though this is a busy time, I like the idea of living life instead of life living me (if that makes any sense).

On the professional side of life, there are a few things in the work for both of us that I am excited to write about once we progress a bit further.


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I have been a blogger for a long time. Even before I started LearnDash, I wrote a blog while in college as I first became familiar with WordPress. Expressing myself through blogging has been a major part of my life.

So, when I first heard about artificial intelligence (AI) written blog posts, I sort of rolled my eyes. Many of you can remember the days of “article spinners” and the garbage output – half of the time they didn’t even make sense. I assumed the same for AI written blog posts and never gave them a second glance.

Until recently, and I must say, AI blogging is damn impressive.

I have spent a number of days the past week experimenting with a variety of AI content platforms to see the type of quality they would produce (finally landing on WriteSonic). My assessment is by no means scientific, but my best estimate is that most of the AI articles I created were about 60-90% complete. Meaning, most of the content is ready to be published without any updates.

To be clear, there were times when the articles were quite poor. This is most often the result of targeting a very specific industry topic that requires in-depth knowledge in order to write about it effectively. But I found that if I took it “up a level” to a more general topic, the quality of the content improved.

Herein lies the opportunity, and the method, in which you can use AI for your own content.

What you can expect with AI blogging.

If you rely on blogging as a core part of your business, then it can be challenging to come up with ideas and post structures regularly. This is where AI can help. When I use WriteSonic, I’m able to whip up outlines in about 30 seconds for any topic by just giving a few prompts.

For example, I put in the prompt Types of Mortgages, and got this outline:

Not bad, right? Honestly, this feature alone provides enough value for most bloggers. I should note that this is just one outline of about six that were presented after I gave my prompt.

This is just scratching the surface of AI content generation. Let’s say you wanted the intro written for you (just to kick things off). Well, that’s possible. Using the same prompt, I was presented with six intro paragraphs. Here is one:

Again, not bad at all! There are definitely some things I would change, but for the most part, it’s good to go and is a great intro to my article.

AI content is best when you keep the topics rather broad (in this example, “mortgages” is a pretty generic topic). If you drill down into a subject further, then you will find that the content isn’t as robust, with sentences that don’t really say anything. For example, I tried Paying off a Mortgage Early as the prompt, and the blocks of text weren’t so impressive.

This was the shortest of the six options presented. The longer ones weren’t any better. They all were essentially just a few sentences being repeated in different ways.

How you can use AI-generated content.

Undoubtedly, there will be people out there that use AI to write their entire blog posts, and without making any changes. It has to be said that the articles that are purely AI written are not the greatest. Even the best ones need a little massaging to sound more natural.

And that’s really the point. A natural sounding article is a good user experience that reflects well on you and your brand. If you are interested in using articles written using AI, then you owe it to the reader to do a little proofreading before you press publish.

If you’re anything like me, you’ll be impressed with the quality of your articles (and how quickly you’re able to complete them), making it tempting to just publish them as-is. But as my friend Jack points out in the tweet below, you’ll want to be approach this strategy with a bit of caution. Google doesn’t like this kind of content, and if they can figure out how to accurately detect it, they’ll penalize sites with AI content.

So if Google will potentially punish sites using AI-generated content, how can you use it?

Well, one option is to just ignore the threat. There are some major outlets using AI content right now (and they have been for years) – such as the Associated Press. Make some intelligent modifications to the core content, and you’re in the clear (…hopefully).

I am testing this “intelligent modification of AI content” method for my real estate investment business, but admittedly, content marketing is not a primary customer acquisition strategy. If the content was flagged in any capacity, then the business would still function fine. That said, I will admit that it would really suck to lose a potential passive marketing channel.

Another option would be to use AI to help you create an outline for your article, and then you write all the content. This is a conservative approach that should leave you sleeping worry-free at night, and is probably the best way to get started using AI. It’s especially powerful for helping you come up with a good sales page, or product description. Granted, it’s more time-consuming, but it will help you get through writer’s block, which will help you write more efficiently.

Finally, you can just avoid AI content creation altogether. That’s certainly a valid approach. If your business is 100% online, and you really rely upon content marketing for customer acquisition, then not using it is the safest way to avoid any potential penalty. Either write the content yourself, or hire someone to do it for you.

AI content will only get better.

Something that we all know about AI and machine learning is it continues to improve over time. I think this may start to create a cat and mouse game between purely AI-generated content and Google.

If I have learned one thing in my career, it’s that you don’t want to try to beat Google at their own game. So, while AI content will improve, I highly recommend that you don’t just use the content “as-is”. Humanize it with your own voice and expertise.


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Once upon a time, calling someone on the phone was the way to go for receiving technical support. I can remember being on the phone with Dell all the time because something was always happening to my desktop computer.

Without fail, these support reps would always insist that you turn off the computer, unplug it, then plug it back in. I now realize how that Level 1 Dell support rep was providing the equivalent of a canned reply that gets sent out today for common troubleshooting issues.

In WordPress, this is the equivalent to: try deactivating all your plugins, then reactivating one-by-one until you find the culprit.

Not that anything is wrong with that advice. Given the nature of WordPress, more often than not an issue is the result of a conflict. The problem is that people often do this process on their live site instead of in a staging or developing environment, and this results in additional frustration and angst.

Which actually brings up a point worth mentioning: if you don’t know how to have a clone of your WordPress website on a development environment, then you should not be using a self-hosted version of WordPress. Just go to WordPress.com instead, where you’ll get 80% of the functionality without all the headache.

But by in large, support for WordPress products doesn’t include chat or phone. The vast majority are ticket based, with some still utilizing forums.

At one point or another, I used every method of support (phone, email, forums, chat).

In the early years of LearnDash, a forum was used to field support requests, with occasional Skype calls if necessary.

That wasn’t sustainable.

I then tried supplementing a ticketing system with chat support. I figured it would be a way to differentiate from the competition. From a pre-sales perspective, chat was outstanding, as I could close multiple sales before lunch. The problem was that after the purchase, these same folks tried to use chat for getting help as well, and they became increasingly frustrated when told that they needed to open a support ticket.

Now, I can concede that some of the support requests were simple enough, so it was possible to just answer it. If the request was more complicated, then I would raise a ticket for the customer. As smooth as that process sounds, it started to create a bottleneck. Also, I found that these individuals had different expectations about the time to resolution for their issue (often wanting same-day service). They would continually open chat again to check on the status.

What I noticed was that the chat functionality actually slowed down the entire support process as it created an extra, unnecessary touchpoint. If this was just one or two people, then it would probably be no problem. However, LearnDash is not some small-time plugin. Some issues are very complicated and require a lot of digging to resolve given a customer’s particular WordPress configuration. And therein lies the issue.

The WordPress business model is not a feasible environment for offering chat support.

In the world of WordPress, one of the largest cost drivers for a company is support. A popular WordPress company needs more people working in support than a SaaS – plain and simple. Why? Because the WordPress value proposition requires it.

Everyone wants their own unique WordPress configuration, but the reality is that not everyone is good at it. They’ll install duplicate plugins, never update the site, use garbage hosting, and so on. Inevitably, this increases the chances of something going wrong.

Support reps have to learn about the issue within a different context for every support request. This takes a lot of time from very skilled individuals. Multiply this by hundreds of tickets per day, and you can see why WordPress companies have so many folks working in support.

If you want chat support, you’ll have to pay at least $1,000/year.

Offering responsive chat support with so many unknown variables about the environment, and at a cost of just a few hundred dollars per year, is just plain bad for business. That may look different though if the everyday WordPress user is cool with paying a minimum of $1,000 per year.

For some, that expense might be worth it. In fact, I once considered offering chat support for that price as one of the purchase options for LearnDash, and I am confident that it would have been chosen by a segment of customers. The customer gets the chat support that they want, and the company gets more money. That sounds like a win-win, right? No. It’s not. It would have still been a loss to the company, especially at the low $1,000 price point.

First, if you have customers from all over the world, then you need to make sure that they receive the same amount of chat support time. This essentially means that support would need people working around the clock. Not just support people, but mid-level management as well to oversee these folks and to help with escalations. These employees then have to interface with leadership (the bulk of which working in U.S. timezones). The logistics get muddy, fast.

Secondly, let’s not forget that the vast majority of WordPress users do not have $1,000+ to spend on a single plugin, and as such it simply does not make sense to build out an infrastructure to support only a minority of the customer base.

For a business to realize profitability of chat support, they need to build the business around that offering to take advantage of efficiencies of scale. Bolting on live chat support as a “feature” is the opposite of this. It creates far too much overhead.

As long as WordPress businesses care about being profitable, they will not offer chat support – and that is in your best interest.

Listen, I get that there are people who really want chat support. You may be one of them! But you know what you also want? The teams that build the software to remain in business.

It’s Pareto’s principle, and it’s in your favor.

In exchange for an insanely low price, you get enterprise level software, continual development, and competent support on an insanely complex ecosystem of software. The only cost to you (aside from low license payments) is that you don’t get chat support.

But if more support is something you prefer, then my advice would be to take the money that you saved by not paying $1,000/yr for a license and hire a part-timer from UpWork to help out if problems do arise on your website. Let them handle the entire resolution process, and allow them to open tickets with the various support desks if necessary. This way you get white glove support to all the plugins on your site, not just one.


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After the holidays, Lorena and I were pretty wiped-out from the travel. We hopped between five different places in just a few weeks, and the added stress of the COVID spike drained us mentally. When we got back to Austin in January, we were content to stay in one place for a while.

Earlier in March we took a short trip to California to look at some homes for sale. That trip was nice for a variety of reasons, but I didn’t sleep too well. Our AirBNB had paper thin walls and floors, and every night the person living below us snored so loud that I had to sleep on the couch in the living room.

So aside from that small trip, we have been in our routine in Austin, and at this point we feel ready to travel again to see family.

The realities of living far away from family.

When we feel the desire to go see family, Lorena and I try to plan our trips so that we can see several people in one go. This often means that we are on the road for extended lengths of time, which in of itself is not so bad, but does often lead to the burnout that we experienced at the end of 2021.

But this is the reality of living far away from family. Instead of short trips, we do extended visits in “batches” numerous times a year.

For this trip, we are headed to Connecticut, Michigan, and Ohio. We then have a short break in Texas before heading to California followed by Mexico.

This family circuit will bring us to early summer, at which point Lorena and I will probably take a moment to catch our breath in Austin before plotting out our next travels. Which, if I’m honest, will be pretty quick since the summers in Texas are absolutely brutal.


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WordPress has been a part of my life in one form or another since 2006 when I started my first blog on WordPress.com. I went from a user of their hosted service, to self-hosting websites for family and friends, to starting (and eventually selling) a premium plugin company.

The WordPress web is everywhere. I can’t help but notice when websites are running WordPress and one of the hundreds of plugins that I know…

“Oh, I bet this site is using Gravity Forms…”

::checks source code::

“Yup. There it is.”

Despite its obvious flaws, WordPress is still the best no-code platform for building a business – I would never argue against that. But as I look at what may lay in store for me in my career, I really don’t see myself working in WordPress anymore. In fact, I question whether I want to be in tech at all.

Seeking inspiration outside of tech.

Something that I know about myself is that I tend to gravitate to projects where I can express my creativity. I find joy in the process. Building and growing something (a product & brand), and ultimately automating as much as possible so that it is no longer dependent on me.

This expression of creativity is easy to accomplish in tech, and in my case, WordPress. Well, at least it used to be.

The reality is that I am burnt out from WordPress and have been for some time. The challenges of the industry aren’t something that excite me anymore. I will always be a user of WordPress, but I think I need an extended break from working in the space.

To be fair, I am pretty much out of it already. I am involved with LearnDash still as an advisor behind the scenes, but that role doesn’t fill up my time. I do have bi-weekly WordPress-focused conversations with my friend Ross Johnson at NoFilter.fm, but I wouldn’t really count that as working in the space. It’s just a venue for casual reflections and sharing of success stories in the hopes of helping others.

I have thought about the possibility of getting into a SaaS project. That sounds like a fun challenge, but the more I think about it, the more I know that the fast-moving world of software will bring with it the same stresses that I had in the past.

I know the mentality that it takes to deal with things like security issues, constant new competitors, disgruntled customers & employees … and frankly, I’m just not there. Maybe one day I’ll feel up for the challenge again, but after nearly a decade of dealing with the negative aspects of software, I just can’t bring myself to do it.

All this is to say that I’d rather be a customer of tech solutions, not offering one.

Keeping busy, and keeping an eye open.

At present, I am helping Lorena with her online courses. I must say that I really enjoy that process for a variety of reasons, but mostly because of what I mentioned earlier: my love for the building and selling process. I honestly can’t get enough of it and feel grateful to have the opportunity to continue selling online.

In addition, I am also exploring non-tech related projects that may excite me. I am still trying to figure out what that is, and if I am honest, it can be frustrating at times as I am eager to start with something, but I just don’t know what at this point. I have to remind myself that this is okay because I know that these things can’t be forced. At the same time, they don’t just come out of nowhere. A little effort is needed.

After selling software, I am finding the “old-fashioned” industries to be quite appealing. Real estate, for example. I also like challenges, and an industry that is outside the tech space will test my entrepreneur skills in new ways. I have always thrived when I had to “prove people wrong” (even if only proving it to myself), and getting involved with a different industry gives me that opportunity.

Wherever I land, you can bet I will be documenting my journey here on my site. And while I don’t intend to work in tech for the time being, I will still be offering insights and opinions for entrepreneurs in this space (especially as it relates to WordPress) as I think there is value for others in sharing my honest, experienced-based takes.

And who knows, my path may lead me back to tech at some point. Possibly, even WordPress.

#WordPress #happiness

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It’s a few months into 2022, and we have booked our first trip!

Instead of one of our planned travel destinations, Lorena and I have decided to head out to SoCal for a last minute mini-getaway. This came about rather suddenly, which made it exciting to plan in just a few hours time.

This is the result of both of us were feeling like we needed a little break from the everyday routine and location. The recent weather in Texas hasn’t been doing us any favors either as it has been gray, rain, and chilly for the entire week.

So, to cure us of these blues, we’ll be heading to southern California for a little sun and a change of pace. We’ll be looking at a little real estate while there as well – because, why not? We won’t be in Texas forever, so we are keeping an eye out for inspiration.

We booked our Airbnb in Orange County and will be exploring the beach towns that it has to offer. And I must admit, I am looking forward to hearing, seeing, and smelling the ocean!


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