Spanish Improvements

August 2, 2026

Key indicators that I am still improving.

I've been studying Spanish since 2020. Those first three years were tough, but now I'm fluent. Not perfect, but fluent. Honestly, I feel like I reached my ultimate goal and it feels great.

I don't study anymore, but I just try to use the language when possible. This primarily means reading books in Spanish, having conversations (mostly with family), and watching Spanish shows on Netflix. I also make a point to have one to two “lessons” with a tutor from Mexico each week, but it's just us chatting about life.

My progression is a lot slower now in the language. I have my habits now, and I'm not trying to study industry-specific vocab. Everyday language is more useful for me living in California.

But I'm still improving nonetheless. Ways I know:

I catch sarcasm. This is a big one because sarcasm is difficult to detect when you're learning a language. I don't get it all the time, but more than before.
I use new words. When I learn a new word, I make a point to use it as soon as possible in conversation and commit it to memory. I get this opportunity when I'm with family.
I've lost the fear. I don't have any fear when meeting someone new and having a conversation in Spanish. Sometimes accents can be tough, but I manage and it's not a biggie. I'm confident that we'll be able to communicate.
Phone conversations are easy. Talking to someone in Spanish on the phone used to be the most intimidating part of the language. Now, I can have normal conversations without needing the visual cues.
Passive listening is easier. I'm able to “half listen” to conversations in Spanish and then fill in the gaps. Not as well as English, but still an improvement from when I had to focus intently to understand everything.
Lorena asks me for the correct word. Sometimes Lorena will forget a word in Spanish and ask me mid-conversation (and I'll know the word she's searching for). That's pretty cool!

My continued improvement in Spanish isn't like it was before with very obvious leaps, but the incremental changes I'm making now are far more exciting and motivating to me because they represent the language becoming more intrinsic to me as a person.

#personal

Give Creativity Some Space

July 19, 2026

Give creativity room to breathe, and happiness will follow.

I consider myself to be a creative person. Not in the sense of painting pictures, sculptures, or drawing, but in the world of business. I've said it before, but being an entrepreneur is my art.

But like any artist, I can't be satisfied if I don't have the space to fully express my creativity. This used to cause me a lot of stress in that if I didn't have that mental space, I would feel constrained and frustrated. But my perspective on this has shifted over the past few years.

Part of being an artist is recognizing the environments that are conducive to creating art, and waiting for the opportune moments. In other words: not forcing it. I used to force it. I used to still push to be creative even when life was choking out the space for that creativity.

Sitting with the Moment

Currently, I don't have the space to be creative. The schedule I have with my newborn doesn't leave much time for anything else, let alone high-level creation. I'm tired and I'm restricted to a schedule that isn't really within my control.

Rather than get frustrated at my inability to pursue creative thoughts, I just take stock of where I am in life and I “let it breathe”. Meaning, I stay firmly in the moment and recognize that it's not the right time, but that time will come. Accepting it and moving on.

With this approach, fulfillment comes from timing. Give creativity space, and happiness will follow.

#happiness

Price Raises and Loyalty

July 6, 2026

Why not raising prices on existing customers can be good for business.

The other day I was on X and I came across this post from my friend, Matt:

I think we can all relate on some level. Price increases have become an expected part of life. Matt mentioned how he raised prices at The Events Calendar during his time there, and it made me think about what I would do today if I were running a software company and wanted to raise pricing. Honestly, I'm on the fence.

On one hand, I get the reason for raising prices on legacy customers. Costs go up over time, especially if new functionality is implemented into the plans that are resource intensive. It only makes sense to cover those costs and there's nothing inherently wrong with creating more profit. The backlash on doing so today would be significantly less than in 2016. For better or worse, people are used to prices going up.

But that's precisely one reason why I would consider not doing it.

Standing By Your Customers

As consumers we are getting absolutely beaten down by the subscription economy. Every little thing is being used as justification to raise prices. Heck, sometimes there are no justifications given at all, just a higher price issued by the higher-ups because the boardroom wants to see bigger margins (I'm looking at you YouTube TV).

I'm a believer in doing well by doing good. If it's feasible, I think locking people into the rate that they buy in at (as long as they maintain an active account) falls into that category. Even more so now than 10 years ago. Brand loyalty is difficult to buy, but one way you can do it is by honoring the contracts you make.

If you do decide to raise prices, give people a long enough runway to prepare mentally for the shift – don't just throw it at them. For example, this could mean letting their current contract period end (one year from initial sign-up) before new pricing goes into effect. Also, give them an offramp should they decide they need to move on. If a few folks write into support saying they cannot afford it going forward, give them an extra year at legacy pricing.

In other words, just be human about it all. Nothing is worse than the heartless corporate decision-making that we have become accustomed to today.

#entrepreneurship

Plugin Security Will Sink WordPress

June 25, 2026

The biggest “black eye” in WordPress will be its downfall if things don't change.

Let's get the obvious out of the way: I'm not a developer. So, if you're looking for technical solutions in this post, then my apologies in advance.

Okay, cool, we're on the same page.

I've been out of the WordPress product space for coming up on five years. There are parts of it that I miss, but one thing that I don't miss is the security issues caused by plugins. No plugin is immune to them, either. When I ran LearnDash, we had some security scares. It sucks for everyone.

The good news, for years, is that plugin providers have always handled these issues with reasonable speed and minimal negative outcomes. Not all, but most. The community was really proactive about staying on top of such things.

I'm not sure if this is as feasible in the AI era of today.

WordPress 7.0 Highlights New Dangers

Roger Montti from Search Engine Journal wrote a thought-provoking article (and inspiration for this post) related to WordPress 7.0's AI API keys and the rush it will cause for attacks on vulnerable sites. I agree with the threats outlined. It's a very real possibility.

At this point it looks like the WordPress space is just treating it as “business as usual”. It's this approach that will ultimately lead to WordPress losing even more market share.

AI is fundamentally changing the speed, scale, and sophistication of attacks against WordPress sites. Instead of automated scripts, AI can adapt, optimize, and move forward with attacks in ways that we haven't seen before. By way of example, Patchstack (cited from the SEJ article) suggested that exploitation from high-impact WordPress vulnerabilities is just five hours now.

WordPress already suffers from the “insecure site” reputation. If things continue as they are, it'll only get worse. A lot worse.

What Should We Do?

Remember how I said I'm not a developer? Okay, this is where that matters. I'm not good at providing technical paths forward, but I'm pretty good at recognizing business threats and opportunities.

This threat has always existed in WordPress, sure, but not like this. It's going to get worse if nothing is done to improve it. What I want to know is what is being done currently? Because from my perspective, it looks like the issue still gets punted to hosts and plugin devs.

I'd love to see real leadership in this area. Not just information sharing or “best practices”, but actual think tanks resulting in coded solutions that drastically help mitigate this increasingly embarrassing issue. We could start by assessing the criteria for being listed on the repo. Could we implement AI security hardening to monitor and verify the code of any plugin submitted and hosted there?

Yeah, I get it, that's likely not feasible given how expensive it would be, but these are the types of conversations that I'd like to see happening. Maybe they are already, and if so, great! WordPress can't drag its feet here.

Learning from Others

Say what you want about Emdash, but at least they are attempting to tackle the issue because they know how real it is. Their way forward isn't really the “WordPress way”, I get that. Though I think we do WordPress a disservice by just flippantly dismissing their technical approach and moving on with our heads in the sand.

Something I found interesting was reading the comments on their social media when they came after WordPress. The sentiments were largely the same, and leading the way was the growing downside of the plugin ecosystem. What is often cited as WordPress' greatest strength is being seen as its most glaring weakness.

The Inflection Point

The WordPress project is at an inflection point. Over the next year, it is critical that it move deep into AI adoption and enablement, and that includes bolstering things from a security standpoint.

For me, I won't host another WordPress site in the traditional sense. Why? Because I'm not trying to be a security pro with my simple websites. No time for that nonsense. I like the static options like SimplyStatic Studio (I transitioned a website to it and love it). Aside from that though, I actually see more benefit in just using something like Loveable and hosting everything there for the added AI features.

Progress is Being Made

The good news is that WordPress is making strides with AI. It's not yet widely known or advertised, but things like Jamie mentioned below are precisely what the project needs.

Let's hope that things keep going in this direction, and that more emphasis on security starts to emerge. To date, it's not very user friendly, at least not compared to tools like Loveable. I anticipate that this will change over time.

Cautiously Optimistic

Overall, I'm optimistic about WordPress evolving in the ways that matter. The community voices are loud and clear. It's up to Matt to set the priorities. Hopefully, he's not too distracted with his WPEngine lawsuit to do what is right (and needed) for WordPress as a whole.

I'll revisit this in a year to see where things have landed. By that time, I think there will be some clear market signals one way or another.

#WordPress

No Time for Anything Else

June 16, 2026

Diaper, eat, sleep - repeat!

Since becoming a dad, I've had no time for anything other than baby stuff. You know, the usual diapers, feeding, napping cycle. It's weird, because while it does get draining, in a weird way I also enjoy not having time for extracurricular stuff. It keeps life small.

Everything is intentional right now. Tiring, but intentional. We are trying to make sure our daughter has everything she needs to grow strong and healthy. The first couple of weeks are a little stressful as we try to make sure that she regains her birthweight. That actually taught us something as new parents.

Trusting Our Instincts

At our first pediatrician appointment a few days after birth, the doctor was concerned at our daughter's weight loss (which was at 8.4%). She wanted us to take up an aggressive feeding schedule supplemented by formula.

Typically, 10% is where it's a serious concern, so we were still within the acceptable range. Still, this brought upon undue stress. We spoke with some other medical professionals, including our midwife, who were less concerned.

In the end, we avoided formula and augmented our feeding schedule accordingly to turn things around. And turn around they did as our little one met and then exceeded her birthweight.

Staying the Course

We still have to maintain the regular 2-3 hour feeding schedule so that she eats roughly eight times per day. There are also more doctor appointments in our future.

Becoming a dad is a shift that I'm still getting used to. I'm learning that newborns require a lot of constant attention and effort. The interactions are one-dimensional at this point, which is to be expected. I look forward to the days when she starts to smile at us intentionally. Something tells me that'll be the best.

#personal

I'm a Dad

June 8, 2026

Entering a new era of life.

Recently, Lorena and I welcomed our beautiful daughter to the world.

I'm not even sure how to put my feelings into words. “Happy” doesn't even begin to describe what I'm feeling. I'm overwhelmed by joy and gratitude, with a sprinkle of nervousness as well. I'm so in love with this baby girl. She is everything.

I'm a dad. I never thought I'd get to say that. It feels so good.

#personal

One Year Later

May 21, 2026

Reflecting on the past year of my entrepreneurial sabbatical.

Last year around this time, I decided to walk away from coaching. I informed my clients, completed my final sessions, and then closed up shop for good. The truth is that I enjoyed coaching, but I was just done. And not just from coaching itself, but from all things entrepreneurial. For the first time in my life, it was time for an entrepreneurial sabbatical.

I didn't know what to expect, but I certainly wasn't expecting it to be so challenging. Especially in the beginning. But it makes sense as I have been in the entrepreneurial mindset for decades. It wasn't something I could just “shut off” overnight.

As time went on, I started to settle into the slower pace of life. I focused on quality time with my wife and family and really integrating myself into where we live. I have started to appreciate the smaller moments. The simple things. Stuff that I would otherwise have ignored if I were working on my own project. I even had the opportunity to be a guest lecturer at my alma mater which I really enjoyed!

Where Things Stand

I'm getting the itch again, but I'm not ready to scratch it just yet. Life has a way of shifting priorities and right now I'm locked into some personal journeys. But that will change at some point. Because while I've stepped away from pursuing entrepreneurial projects, it hasn't stopped me from thinking.

So, I don't know exactly when, but I can tell that I am closer to the end than the beginning of this much-needed sabbatical. When it does end, I'll have a renewed sense of energy and clarity. That was the point of the sabbatical in the first place, and it seems to have worked.

#entrepreneurship

I Gave a Guest Lecture

April 22, 2026

Actually, I gave two.

A couple of weeks ago, I had the opportunity to guest lecture at the college I went to for undergrad. It was actually the second time I had the privilege, and this time it was on my favorite subject: marketing & advertising.

I get so energized when talking about this kind of stuff. I guess there is no better way to describe it other than just plain old fun for me.

Admittedly, something is kind of lost when you're having the class virtually on Google Meet, but I think I managed well nonetheless. Even got some laughs out of the notoriously difficult-to-entertain Gen Z.

In the future, maybe when I'm in my 50s, I could see myself teaching in higher education to pass on the insights and skills that have helped me in my life.

But not yet. I still have things I want to do!

#personal

WordPress Plugins are in Trouble

April 13, 2026

Some WordPress plugin businesses won't survive this.

If you spend any time on social media, you'll see that revenue is coming down for WordPress plugin businesses, and who knows where they'll bottom out. Honestly, some of them are screwed, and it's not looking good for others.

For as long as I can remember, the defensible position for most plugins has always been:

Feature gating
Add-ons
Support

There are others to consider, but these have always been the main reasons why you'd renew a license. Today, Claude (or pretty much any AI offering) sorta makes them less critical.

For example, consider a plugin that revokes access to certain settings unless you have a valid license code. Or, one that shows a constant license nag on your dashboard. Well, now you can just whip up Claude and tell it to remove the code that does this and you're done. You don't have to be a developer, it just takes a couple of seconds.

For add-ons, it does sort of depend on the scope. Those that add simple integrations are no longer a necessary buy. Why pay extra to connect to Mailchimp when AI can just whip up a mini-plugin for you? Pretty much any connector add-on is a quick fix. Okay, it's perhaps a tad longer if you're not a developer through trial and error. But if you have a client and you're a dev, you can save your client money by just having AI build out the connection really quick.

There will always be a need for support, but less so now when you can just ask AI for help to troubleshoot something. This is especially true for plugins that are more of a utility. Now, on the other side of this is that many plugin companies are using AI to help them give better support. Of the three, this one is the area that is still a strong motivator to renew a license, plugin depending.

Now What?

You know, I don't have a definitive solution for this one. I don't think anyone does as the market sands are still shifting. AI has really challenged the status quo of tech.

For me, here are the areas I'd be thinking about if running a WordPress plugin business:

Community

AI can't recreate it. This is a wedge. This is why someone will want to renew. Many plugins have big communities but they are an afterthought. Some even consider them a burden. It's time to make it a top priority. For example, I would start evaluating the utility of adding a Slack or Discord offering. Or, potentially investing more heavily into a FB group if it already exists.

SaaS Certain Features

Look for the areas that create the most support and try to find a way to make those a SaaS to improve user experience, dependability and to reduce headaches for both you and your customers. If you're hung up on keeping that part of the code open source, you can still do so if you want (though it's not necessary).

Invest in New Marketing

Blogging is still worth it, on some level, but if that's all you do then time to move into new areas. Connection matters, and for the moment, YouTube is how you do that. I'd invest heavily into YouTube to bring about the human element in an AI world (this goes back to my first point on community).

WordPress Isn't Going Anywhere

This is not the “death” of the platform by any means. New avenues are going to open up, and that means for WordPress plugins as well. This is just a market shift, and there will be some growing pains along the way. For some, this means the end of their business. That's the nature of the free market.

#WordPress

Thinking About What's Next

March 4, 2026

I'm taking my time to figure out what is next for me, and when.

When I sold LearnDash, I agreed to a non-compete agreement, which is pretty standard for any business sale. Mine was a bit longer than normal, but I didn't mind (and still don't). If anything, it has forced me to take a giant step back and to get in tune with what it is that motivates me.

But it wasn't always so easy. Immediately after the sale, I took up various projects because I was so used to the “go-go-go” frame of mind of an entrepreneur. I had no practice at slowing down.

But the non-compete forced me to eventually slow down.

I slotted into coaching for a bit, but it's not something that I ever planned on doing forever. Don't get me wrong, it was enjoyable.

The problem, however, was that it lacked something very central to what I like to call my “flow state”. That feeling where what I am doing doesn't feel like work. Coaching lacks a competitive and creative outlet that I crave.

I Thrive When Competing

Ever since I was five years old, I have loved to compete.

I played every sport as a child, and eventually took to soccer, where I continued playing through college. I competed at a high level, and I loved every bit of it. The trials and tribulations. Winning. Hard work. I found that these qualities transfered very naturally into entrepreneurship.

In 2013, I launched LearnDash and created the entire WordPress LMS segment. That same year, I gave up playing soccer (forced due to a neck injury) and put every ounce of my energy into “winning” in my market, as it was quickly flooded with other players.

The wins weren't always fast or easy. Some required the long game. Years and years. But I don't give up. Ever. I will never be outworked or outlasted. It's my superpower as an entrepreneur.

I don't get intimidated, but energized. If a competitor does something good, I can't wait to clap back ten-fold.

But I've softened as I've aged.

At 28, I was a different person. I viewed business in black & white, but with more experience and perspective, I've softened my approach to competition.

It's still “us versus them” (it is always in business), but I wouldn't villainize my competitors like I did in the past.

This perspective, one that comes with the passing of time, is an asset. Because let's be honest: always being ready to “fight” is stressful. I was constantly on edge, and it impacted my health. It, in part, led to my increased drinking.

If I were doing it all over again, my view would be more refined. Still up for the challenge, but seeing it more as a game rather than “life or death”.

I Crave Creativity

Competition for competition’s sake is well-and-good, but it isn't the only thing that I need. I need creativity. I've said it before, but entrepreneurship is my art.

I thoroughly enjoy the building blocks of a business:

Creating email marketing campaigns
Brainstorming ways to position a brand
Product enhancements to gain an edge
Long-term product strategies
Creating solutions that customers love

These activities are like my drug. I get high from doing them, and then high again seeing the impact that they can have on my business. Tying it to competition, these activities take on more meaning. I'm more motivated and the end result is more refined.

When I do these things, I'm in my flow state. I'm vibrating on a different level, and it just feels right.

So What's Next for Me?

I'm still gaining clarity on the two areas above. My current sabbatical has been extremely helpful so far in creating the mental space I need at this point in my life.

I guess what I'm trying to say is that I'm not rushing anything. In fact, I can't anyway with my non-compete in place. This matters, because I don't have interest in just any niche. I love the e-learning space. I've worked in it since 19 years old. In many ways, it's all I know.

#entrepreneurship