Investing in Value

I got my start making “real money” at 19. I had discovered the world of arbitrage and applied it to the web, buying low-cost traffic through Google AdWords and directing it to sites displaying higher value ads via Google AdSense, then profiting on the difference. For a few months, I was rolling it in.

It started to bug me, though. I didn’t feel like I was creating real value. Folks would visit my sites, looking for solutions to their problems, only to then be directed to other sites that may or may not help. I was just a middleman, profiting on the difference.

Not too long after, I got out, walking away from what was at the time a fantastic income, and feeling no regrets. I ended up taking the most popular “niche” I’d discovered (getting rid of mold) and launched a blog focused on the topic, where I was able to provide real value.

New Opportunities

Fast forward to yesterday. Earlier in the week, a new friend of mine who day trades as a hobby gave me a heads up about Robinhood’s pending IPO. My prior experience in day trading was limited, at best.

We talked about it, I did some light research (including reading their S-1), and hypothesized that it would be reasonable for Robinhood to IPO and see a gain of 20%+.

I placed a bet, planning to “flip” once it hit 20%.

Mental Fitness

One of my favorite books of the past year has been Shirzad Chamine’s Positive Inteligence, which focuses on developing mental fitness. A key aspect of developing mental fitness is not letting your saboteurs (which trigger feelings of fear, worry, anxiety, etc) run the show.

That’s what I want. Feelings will come and go and they’re helpful, bringing risks and opportunities to my conscious attention. What I want, though, is live from a place of positive response, choosing curiosity, empathy, focus, etc., to respond to the opportunities that live sends my way.

The past 24 hours gave me a front row seat to a wide range of different emotions. I was excited, nervous, unsure, sure, then unsure again, curious, empathetic, uncertain, and on. I also had a hard time falling asleep and woke up early.

Lessons Relearned

Robinhood IPO’d this morning and didn’t make 20%. I sat there for a minute or two, watching the price jump up and down, feeling an accelerated dose of emotions.

I sold my stock, accepted the loss, and walked away.

What I love about the experience is the reminder that that’s not the kind of investing I do. I want to create value and be rewarded for that value.

I respect the folks who put in the time and effort to figure out the day trading game and I recognize that there is potential for value to be created in the process. It’s not the value for me, though.

I want to invest my efforts and energy into opportunities where all that I bring to the table can influence the outcome of my investment and increase the likelihood of significant value being created, for all involved.

All told, my experience with Robinhood was an inexpensive reminder. Now on to better investments.

An App Store for WordPress

In the Benefits and Tradeoffs of Decentralization I wrote about WordPress’ nature as an open source operating system and the decentralized ecosystem that has grown around it.

WordPress as an Operating System has three key audiences:

  1. Creators – The folks who bring their ideas to life on the Open Web.
  2. Extenders – The folks who build tools and offer services that creators use.
  3. Hosting Providers – The folks who provide infrastructure to support and scale WordPress.

While each of these audiences enjoys the benefits of decentralization, they experience the tradeoffs and as WordPress grows those tradeoffs create more problems.

The Problems

For WordPress to continue to grow and succeed as an operating system, it needs to serve each of its key audiences well. Those audiences, though, each face a growing stack of problems related to WordPress’ decentralized nature.

For Creators

While they enjoy a sense of ownership and numerous options, creators often feel overwhelmed with the high volume of choices. They struggle to make good decisions with the choices available, resulting in frustration, stunted creativity, and a higher risk of leaving WordPress.

For Extenders

While they enjoy the benefits of a low barrier of entry and autonomy in development, extenders feel the consequences of low standards and struggle with the sustainability of the businesses they’re trying to create.

For Hosting Providers

While they enjoy the benefits of engaged customers and the associated investments into WordPress, hosting providers feel the pain of increasing support costs and shrinking margins.

Defining Success

My hypothesis is that the tradeoffs of decentralization can be mitigated, without compromising the benefits. To identify a potential solution to the problems of decentralization, let’s start by defining areas of success for each of the key audiences.

For Creators

We want to empower creators to bring their magic to the Open Web with WordPress. Accordingly, in context of the volume of options and the struggle to make good decisions, success includes:

  • Better Options – Make premium plugins, themes, and blocks with sustainable business models available to creators.
  • Better Decisions – As the number of options increases, empower creators to make better decisions.
  • Continuous Improvement – Keep making the Operating System better for creators, lowering the barrier of entry while expanding capability.

For Extenders

We want to empower the folks extending WordPress by increasing their efficiency and effectiveness in development and by supporting and facilitating sustainable business models. Accordingly, success includes:

  • Accessible Standards – WordPress offers a developer portal and Coding Standards. Give extenders tools and resources that make following best practices more accessible, especially for those new to WordPress.
  • Systematic Compatibility – Give extenders the ability to automatically test their code for compatibility with other plugins, themes, and blocks.
  • Better Distribution – Help extenders building businesses in WordPress get in front of a larger audience and offer them better options for engaging with that audience.

For Hosting Providers

We want to support the hosting providers supporting WordPress. As the size and capability of the WordPress ecosystem increases, so do the support costs and while there’s more and more creators investing in WordPress, it’s difficult to find ways to align with that investment. Accordingly, for hosting providers, I suggest that success includes:

  • Reduced Costs – If we can give creators better options and help them make better decisions while also supporting sustainable business models for extenders, we can reduce the support and infrastructure burden on hosting providers.
  • Increased Lifetime Value – As creators and extenders connect, there’s opportunity for hosting providers to be the facilitator of that connection and increase the lifetime value of that creator for the hosting provider.
  • Better Differentiation – If we can democratize more of the key pieces of WordPress infrastructure while reducing support costs and increasing lifetime value we can level the playing field among hosting providers and give them an opportunity to focus on better differentiation for the creators they serve. All hosting providers should be fast – better differentiation in my mind is value added that’s focused specifically on the audience they’re serving.

Introducing an App Store

WordPress as an Operating System needs an App Store, a centralized marketplace where creators can purchase plugins, themes, and blocks in a way that supports sustainable business for the extenders who build them and the hosts who facilitate the connections.

Here are my current thoughts on how it would work for each of the key audiences.


The App Store would be either pre-installed by their hosting provider or installed separately and sit as a layer over the existing plugins, themes, and blocks interfaces. It would offer:

  • Integrated Access – Creators would be able to purchase premium plugins, themes, and blocks right from within WordPress.
  • Better Results – A better ranking algorithm for search results that includes premium options and helps creators make better decisions, including compatibility.
  • Centralized Billing – Their payment information and purchases would be connected to a centralized “App Store” account, providing security and organization for their purchases.


A centralized App Store can make developing for WordPress more attractive and sustainable for extenders, if it’s done right. I suggest that there are five key components to a successful App Store for WordPress with extenders interests in mind:

  1. Accountability – Ranking algorithms should be transparent and continuously improved in collaboration with the extender ecosystem.
  2. Minimized Costs – The transaction cost to extenders should be within 10-15%, including processing fees.
  3. Aligned Incentives – Sustainable business models should be supported and facilitated that align with the value and benefits of decentralized, open source software.
  4. Reinvestment – Profits should be reinvested into better tools and support for extenders and to improving WordPress itself for creators (which in turn benefits the extenders who serve them).
  5. Ubiquity – The majority of WordPress installations should have the App Store enabled, providing a scalable audience of creators for extenders to serve.

Extenders should feel that they’re working with a marketplace they can trust, that’s accountable to them, that succeeds as they succeed, and that continues to improve up to and beyond ubiquity.

Hosting Providers

A centralized App Store can reduce costs and increase the lifetime value of creators for hosting providers while also offering a foundation for better differentiation.

Reducing Costs

A centralized App Store could reduce costs for hosting providers in multiple ways, including:

  • Support Costs – Compatibility and security related issues are a significant source of support costs. By guiding creators away from resources with compatibility and security issues and equipping hosting providers with insights and objective references, the efficiency and effectiveness of hosting support can be improved and costs reduced.
  • Infrastructure Costs – Poorly written plugins and themes can lead to significant infrastructure costs. By guiding creators towards resources that follow performance best practices and facilitating alternatives for resources with known issues, infrastructure costs can be reduced.

Increasing Lifetime Value

A centralized App Store could increase the lifetime value of creators by providing revenue share on:

  • Purchases – For all purchases, including one-time and recurring, I recommend a 5% share of the total transaction be paid to the hosting provider, drawn from the 10-15% paid by extenders.
  • Advertising – For ads delivered to customers within the marketplace, I recommend a 70% share of the advertising revenue be paid to the hosting provider.

A successful App Store would also increase lifetime value by reducing churn to proprietary operating systems.

Better Differentiation

A centralized App Store, and all of its implications for extenders (including reinvestment in tooling and WordPress itself), would help level the playing field for hosting providers and allow them to focus on better differentiation.

Here are a few examples of leveling the playing field:

  • Shared data – Compatibility and security databases would be shared across hosting providers, mitigating the need for separate databases.
  • Shared resources – Tools developed and insights provided by the App Store based on ecosystem wide usage would be made available to hosting providers.

With shared data and resources, hosting providers can then focus their energy on the unique needs of the audiences they serve and optimizing the value that they provide in a way that plays to the strengths of a decentralized ecosystem and is much more difficult to match by the proprietary, fully centralized operating systems.


A centralized App Store, preinstalled by hosting providers, makes better options available to creators and can guide their choices in a way that increases the likelihood of their success and keeps them creating in WordPress, on the Open Web.

For extenders, a centralized App Store offers a path to sustainable business models and can provide accountability, aligned incentives, and reinvestment as it grows.

For hosting providers, a centralized App Store can help reduce support costs and increase the lifetime value of the creators they serve while also helping to level the playing field and empower hosts to focus on better differentiation against the proprietary platforms.

And for the ecosystem as a whole, a centralized App Store, built on creator choice, can help mitigate the tradeoffs of decentralization without sacrificing the benefits.

Next Steps

I just wrapped up a fantastic year and a half at Automattic (heads up, they’re always hiring) and this idea of an App Store for WordPress is what I’m working on next. Curious to learn more or interested in getting involved? Let me know!

The Benefits and Tradeoffs of Decentralization

WordPress is an operating system for empowering creativity on the Open Web. With 40%+ of the web running on WordPress, WordPress is also an indicator of the health of the Open Web. The better WordPress empowers creators and the extenders and hosting providers who serve them, the better the health of the internet as a whole.

Benefits of Decentralization

WordPress’ nature as an open source operating system, lead by volunteers, and the decentralized ecosystems that have built up around it are a key source of its strength.

WordPress provides the built-in freedoms to allow anyone to do whatever they’d like with it. Of the 28,000,000+ live sites on WordPress, they’re spread out over a diverse range of hosting providers, with the freedom to do what they’d like and to move from one to another.

Decentralization offers three key benefits:

  • Shared Ownership – To use WordPress is to own it. That shared sense of ownership is why people are willing to volunteer and work together towards WordPress’ success. It means that the entire ecosystem is incentivized to care for it and support its growth.
  • Options – If a plugin doesn’t meet your needs, you can choose another. If your hosting provider isn’t working for you, you can move to another. The WordPress ecosystem offers a diverse pool of extenders and service providers to meet the needs of creators.
  • Resilience – WordPress is hard to kill. The decentralized nature of the ecosystem offers a resilience that inspires growth-contributing confidence to those who do business in it and provides assurance to creators building on WordPress.

Tradeoffs of Decentralization

The benefits of WordPress’ decentralized nature have tradeoffs. For each of the main benefits, there is a counterpoint.

For WordPress, the tradeoffs of decentralization include:

  • Decision Making – The tradeoff of shared ownership shows up in decision making. It’s hard (as it should be) to make big decisions, especially as the diversity and interests of your pool of owners continues to increase. An initiative like Gutenberg, championed by WordPress’ co-founder, is objectively positive for the project, and yet has collected thousands of 1 star reviews. A decentralized ecosystem makes decision making difficult.
  • Difficult Choices – The tradeoff of options is difficult choices. It can be overwhelming to find the right plugins in the nearly 60,000 options in the directory today. And for businesses building on WordPress, many of the most popular commercial plugins have to be purchased and installed separately. Understanding your options and making good choices with what you have available is difficult at best.
  • Stagnancy – While WordPress as an ecosystem is resilient and hard to kill, the tradeoff is the risk of stagnancy – a bunch of decentralized pools of water, with minimal inflow and outflow. Innovation can spring up anywhere, anytime, seeing the benefits of that innovation across the ecosystem as a whole, though, is difficult and stagnancy is more likely the result.

Now let’s apply those to the three primary stakeholders of the WordPress ecosystem: creators, extenders, and hosting providers.

Decentralization for Creators

WordPress has been (and may it always be) focused first on creators, the folks bringing their ideas to life on the Open Web. WordPress enabled blogging back when it was difficult and changed the face of the publishing industry. Today, WordPress empowers creativity of all types.

WordPress’ decentralized nature provides benefits and tradeoffs for creators, including:

Ownership – You can create whatever you want with WordPress. It’s yours. There are no limits. Responsibility – You’re responsible for figuring out how to create what you want. It is yours after all.
Options – You have numerous plugins, themes, blocks, hosting companies, and service providers available to help you create what you want. The official plugin repository, for example, has nearly 60,000 plugins available.Decisions – Navigating through the options can be overwhelming and, if you’re buying, you have to find the options first. Ecosystem plugins are big business, yet many of the most popular commercial plugins aren’t available in the directory.
Resilience – Your creations on WordPress are resilient, living when and where you want them to.Stagnancy – Your installation of WordPress can grow stagnant and insecure, if you’re not keeping it up-to-date.

The benefits for creators are strong and we see their impact in the growth of WordPress. The tradeoffs, though, have made renting from centralized, proprietary platforms increasingly attractive.

Decentralization for Extenders

Many of WordPress’ early creators became extenders. They built plugins and themes for WordPress to make it what they wanted and often shared what they made with others. Today, much of the WordPress economy is driven by extenders, creating plugins, blocks, and themes, and building sub-ecosystems within WordPress.

WordPress’ decentralized nature provides benefits and tradeoffs for extenders, including:

Low Barrier of Entry – It’s fantastically easy to get started in WordPress. Decentralized resources and support are readily available and you can see your code in action quickly on any number of environments.Low Standards – There are many ways to extend WordPress and it’s easy to make something that’s insecure and performs poorly at scale. For personal applications, this isn’t a problem, when you’re extending for others, though, it matters.
Autonomy – As an extender, you can make what you want in WordPress. You can do just about anything and don’t have to play by any particular set of rules.Compatibility – Just as you have autonomy, so do other extenders, and the result is often incompatibility from one plugin or theme to the next that frustrates the creator – and the extenders that try to support them.
Business Model Flexibility – A decentralized ecosystem means you can create the business model you want. Don’t like the rules of the plugin repository? Host it yourself.Limited Distribution – If you’re building a business on WordPress, your options for distribution are limited and can be mutually exclusive. You’re responsible, effectively, for your own distribution.

With so many creators building on WordPress, the business potential for extenders is vast. Tapping that potential can be overwhelming in a decentralized ecosystem, though, and often requires a successful extender to be good at a lot of different things, above and beyond their design and development skills.

Decentralization for Hosting Providers

While you can run WordPress yourself, the vast majority of creators rightly choose to work with someone else to take care of hosting for them, while enjoying the flexibility that they can change hosts if they need to. The tens of thousands of active hosting providers we have today are WordPress’ decentralized nature realized in practice.

For hosting providers, the benefits and tradeoffs of decentralization include:

Choice – Creators know they have ownership and, thus, are free to choose the hosting provider they’ll work with. A new hosting provider can offer a better choice and win business. Differentiation – Given the freedom of choice, keeping an informed customer requires a hosting provider to show unique value. Hint: saying you’re the fastest isn’t good enough.
Engagement – Creators who recognize their ownership tend to be more engaged. They interact, give feedback, and refer. Support – Creators who are engaged tend to need more support. They’ll install more plugins and themes, they’ll try things and break things – and turn to their hosting provider for help.
Investment – As WordPress grows, the number of creators who chose to invest in WordPress grows with it. Creators are increasingly willing to spend. Margins – Hosting providers have limited capacity to align with and realize value in areas where creators are investing. Accordingly, margins tend to shrink and require increasing scale to maintain.

Hosting providers play a significant role in making WordPress accessible to creators and they’ve built their businesses on the benefits of WordPress’ decentralized nature. The tradeoffs, though, pose real threats to the sustainability of the hosting provider’s business model, especially in the face of increasing threats from centralized, proprietary platforms.

The Future of WordPress

The benefits of decentralization have contributed significantly to WordPress’ growth as an operating system. Creators have a sense of ownership, recognize their options, and contribute to the resilience of the ecosystem as a whole. Creators also feel the tradeoffs, though, as extenders and hosting providers overwhelm them with options, leading to difficult decisions, and the growing threat of stagnancy as creators stop creating in WordPress.

What if there was a way to keep the benefits of WordPress’ decentralized nature and mitigate the tradeoffs? What if we could offer creators better choices and help them make better decisions? What if we could offer extenders a way to build better software for WordPress and enjoy more sustainable business models? What if we could offer hosting providers a path to better margins through reduced support costs and increased lifetime value?

I believe there is a way and the key is in thinking about WordPress as an Operating System. It’s time to create a better “App Store” for WordPress.

Go With The Flow

I started reading books on time management as a late teenager. One of my first blog posts was about time management! (That, frankly, was embarrassing to re-read – and that means I’ve grown!)

I remember how inspired I felt. I started implementing time management systems and felt like I was figuring it all out.

One book told me to start my day by “eating frogs”.

Another told me to put the big rocks in the jar first, then pebbles, then sand, then water.

Another told me to setup inboxes and work my way to inbox zero.

I tried it all. I was on top of the world. No more procrastinating. I was getting things done, filling my glass jars, and eating those frogs.

The Problem

My time management win streaks wouldn’t last more than a few months. I’d hit a wall, something would fall apart, and before long the system would collapse.

My conclusion at the time, and for years after, was that I just needed to try harder. I needed to exercise more grit, more determination.

There’s something to all that, for sure. It didn’t work for me, though.

As a new husband, I was a few years into my experiments with time management and had just started practicing the pomodoro technique.

My wife called me during a time block to tell me that she was pregnant. I told her that I’d call her back as soon as the time block was done.

I forgot to call her back.

That was terrible. She still agrees.

Time Management Today

I don’t practice inbox zero anymore. My jars are unopened on the shelf and the frogs and I are at peace.

I get a lot done, though. What’s different now?

I think differently about time and about life. My personal time management philosophy today is simply:

Go with the flow.

Two Key Lessons

The application of my philosophy is summed up in two key lessons.

  1. Play to my strengths – What the books didn’t take into account is that we’re all different. That stuff works, it just didn’t work for me.

    I like flexibility. I like variety. I don’t like getting pinned down. Time blocking, rigid scheduling, all of that can work great for a lot of folks – it just didn’t work great for me.

    I had to get to know myself better and figure out how to play to my strengths.
  2. Design an Operating System – We use operating systems to interact with our computers, our phones, our cars, and, whether conscious or not, we use operating systems to run our lives.

    Over the past few years, I’ve invested time figuring out the habits and tools that I need to get things done.

    My operating system includes “tiny habits,” a scattered system of electronic and paper notes, and a few pieces of software to keep light track of “projects” that span longer periods of time.

    The key for me was doing the work of designing. I learned to get to know my strengths and figure out what works best for me.


I have two recommendations to share based on my experience.

  1. Use tools to get to know yourself better – The StrengthsFinder tool is a great resource. My personal favorite is the Kolbe A, which contributed to several significant breakthroughs for me in both my overall thinking and approach to time management. Make use of the tools available.
  2. Design tiny habits to build momentum – Ridiculously small but consistent amounts of progress in the right direction over time is where magic happens. Rather than trying to “fit it all in”, design habits around what’s important to you and build on those. (If you’re curious for some practical examples, check out my (free) book on Tiny Habits)

Managing Time

The great news about time is that we all have the same amount to work with. I’ve noticed that we humans, in general, tend to beat ourselves up about how we use time. It seems to be a fairly universal struggle.

Get to know yourself better.

If you’re in to inbox zero, filling glass jars, or eating frogs – awesome. If not, keep experimenting and design an operating system that works for you.

1001 Days of Pushups

I did my sets of pushups today, just like any other day and nothing felt particularly special about it.

It’s a big day, though.

I’ve now done multiple sets of pushups every day for 1001 days in a row. No days missed. Rain or shine, on a frozen lake, atop a mountain, on a boat, on a plane, wherever I needed to to get the pushups done.

It’s About Momentum

Practically speaking, what I’m doing today, 1001 days later, isn’t a whole lot different than when I started.

On the pushups front, I started out being able to do 1-2 at a time, four sets a day.

Today, I average about 50 pushups a day and if I want to push myself, I can do about 30 in a row without stopping.

A definite improvement, but there’s more to the story.

I chose pushups because it’s a ridiculously tiny habit. My friends laughed. What difference could a few pushups make? I should join a gym or do some real exercise.

They weren’t wrong in the short-term. A few pushups a day wasn’t going to make a big difference to my health.

Because the habit was ridiculously tiny, though, I kept it up.

Then, something magical happened. I had a habit in place and I wanted to experiment with more.

Pushups became building block habits. And they built momentum.

More Tiny Habits

Today, I track 25 different tiny habits that have helped me build momentum across a wide range of focus areas. They include:

All of these are tiny on their own. Easy to get done and really don’t seem like a big deal.

When I add them up, though, I’ve been able to use tiny habits to create significant amounts of momentum over time.

This experiment with tiny habits has been life-changing for me.

And I’m just getting started.