WordPress is Entering its End-Stage Founder Period

I exit Founders for a living.

It takes a special personality to bring something into existence: grit, passion, vision. But most Founders lack the self-awareness to embrace the limitations to scale their creations. That's where people like me enter.

WordPress is entering its "end-stage founder" period. And creations of all sizes - startups, established companies, even thriving enterprises - all approach this extremely dangerous period of their lives where they are forced to confront a basic question:

Is the Creation more than just the expression of its Creator? Or do the countless contributors - customers, partners, users, audiences, etc. - actually matter beyond just being passive recipients of the Founder's will? Having been a Founder myself, it's an incredibly humbling confrontation and the petty petulance that we instinctively feel requires profound soul-searching to decide what future fate we seek for the ecosystems we have created.

It may be surprising that WordPress, the ostensibly open source content management system, or CMS, that powers about 40% of the web's actively visited and tracked websites, is reaching this moment more than two decades after its emergence onto the scene. But when one looks at the typical factors that lead to end-stage founder periods, you'll see we're more or less right on schedule:

End-Stage Founder Periods (3 Ways to Recognize Them)

1. Go-To-Market repeatedly breaks or stalls out. Typified by either flat-line growth, or by inexplicable and un-reproducible growth curves, that cannot be easily understood or truly explained by founders and their teams. Higher than normal customer churn and employee attrition (voluntary or otherwise) are good signs of this. Jettisoning the clients and people who got you where you are demonstrates not just a lack of alignment, but a failure of leadership and direction.

   
   

2. Competitive threats start becoming the focus, and the Founder starts attacking them rather than driving a unique and differentiated vision for their creations. Truly successful companies have no competitors, and see themselves as such, but the first sign of founder insecurities overcoming commonsense is a misprioritization on external players and going after them.

   
   

3. Work becomes suddenly harder, with no signs of stopping. Founders often panic when they do not recognize the shifting landscape, especially when it's the sand beneath their own feet. They revert to the same core tactics they used to build their creations, which aren't usually fit for purpose, and then drive people, processes, and programs to the brink of failure. They will blame others (usually by faux-blaming themselves), and then search for heroes, both within and without, to support their view and try new (but honestly, the same) motions.

There are no heroic saves to the End-Stage Founder problem. The Vision that they set out for their company was either never shared, or not aspirational enough for others to align. In almost 95% of all cases, founder-led companies collapse. Money has only 2 out of 20 reasons to account for failure (see: CBInsights Post-Mortems, 2021-2023). Wildly successful and profitable companies making hundreds of millions of dollars every year can precipitously collapse in ways that, to an outsider, seem bizarre, but to insiders, was all-too-telling.

Scaling Requires the Founder to Exit

All Founders Exit, but not all exits look the same. For some, they leave the companies they founded and go on sabbatical for years to rediscover their purpose, gain perspective through humility, and decide what they would like to learn and how they'd like to contribute before even deciding whether they want to rejoin their Creations. For others, they are unceremoniously fired by their employees, shareholders, or a commercially-driven legal process (such as a hostile take-over, or an investor revolt). A select few will embrace the change, and step back to take a role where they aren't involved in the day to day, but can help listen generously and aspire to support the next generation of leaders.

Every great company outlasts the life of its founder. Most companies collapse with the demise of the founder, because the founder never truly empowered their teams, listened to their customers or the market, and gleamed a fundamental lesson as to why the Founder and their Vision is fundamentally myopic:

You cannot always know your mission (your plan to execute on your vision), but you must always listen generously to the unknowable needs of future clients and communities in the marketplace of ideas. And in that interchange - of putting the customer at the heart of who you are and what you do - do you suddenly discover your new focus, and your Vision becomes alive again in renewed purpose.

This lesson is what fundamentally leads great companies like @Disney to embrace the unknowable future that it is in the business of making dreams come true - leading them to create theme parks, live action movies, and intellectual property across countless lines of production to better drive engagement from generations of customers - whereas not-so-great companies like Hanna-Barbera, who had out-competed Disney for a few years as the number one purveyor of animated entertainment on the planet, never embraced a vision beyond just making great cartoons. And truly great companies, like @Apple and @Amazon , plan for their own founders' exits long before the confrontation needs to be made.

What should WordPress do?

I've serendipitously built a career out of helping companies rediscover their purpose through the eyes of their customers - past, present, and especially future - and in doing so, help reinvent themselves to aspire to be greater than they could possibly have ever imagined through the original single-person concept that the Founder had espoused. Unfortunately, WordPress' founder, Matt Mullenweg, is going down the path of the majority of founders who encounter the malaise of mediocrity borne of their own limited vision: destroying their own creation. And by some views, it may seem to be intentional in an effort to force some sort of heroic breakthrough. It will fail, because remember: there are no heroes in the end-stage of founder-led cycles.

But there is a solution, and it is one that I've been privileged to learn over the past 25 years as a Chief Customer Officer, a Chief Operating Officer, and even interim Chief Executive Officer of startups backed by great private equity scale-ups such as Vista Equity and Insight Partners or fueled by investor-conscious market-driven forces. And it's to listen.

(I share this forecast and advice knowing full well that WordPress and Matt Mullenweg will likely block me, despite the fact that I, like so many of the hundreds that they have (or really, he has) blocked, helped build this ecosystem and ushered in thousands of organizations and millions of users to WordPress over the years. This tyrannical block-fest is part of the myopic Founder's last throes before ultimately being displaced into a new normal.)

1. Do not turn on your people. Your clients, team members, and partner ecosystem are delivering valuable feedback. Don't take it literally, and study it generously. And especially, do not turn on the people who have helped you breathe life to your creation. Doing so will only accelerate their exodus from your orbit, realizing that according to its creator, the WordPress creation doesn't live beyond the Founder's fulcrum.

   
   

2. Step the Founder back. Launching a desperate public relations offensive against WPEngine has emboldened and granted tremendous credibility to detractors when you should actually be building the space for your promoters (and even passives) to start taking control of your creation's future. Moving away from the day-to-day and handing over the operation to a tried-and-true professional can be tempered with a Founder's continuing directional vision-setting and future-casting in a way that doesn't disrupt, but just contributes on equal-footing, the creation's continued evolution. (This is what has recently been termed "Founder-Mode," to allow a modest contribution to strategic direction without overriding the operational agenda of your executives.) For Matt? A Chairman, or even better, Chairman Emeritus role, will be best at this time. Longer term, it may be time to sell Matt's controlling stake to prevent the Founder's impulse to intervene and impose their imperium upon others. It does not end well, always. It will always rear, after all, as Matt has recently told The Verge: "WordPress just belongs to me." And indeed, with that attitude, it is destined to never be more than his plaything.

   
   

3. Reinvent. This crisis would have never come about, honestly, if the original Founder's Vision hadn't met its logical end. The Web has reached mature saturation: the economics have been largely optimized, and now the very essence of what created the fertile soil on which WordPress was founded - user-generated content with view-driven community-building - has been exposed as, sadly, without much commercial value. Artificial Intelligence, especially generative AI, is creating a new generation that is rendering much of the web and its knowledge largely unusable. There isn't much of a future for WordPress, or any traditional content management system, that doesn't prioritize a new form of knowledge sharing and content discovery that is largely immune from the flotsam of fabricated misinformation. But if WordPress can make the leap to a new modality, a new medium, and side-step the mobile wars and AR/VR search-fest, it could become a new brand that transcends - rather than is defined by - the crisis in which we find ourselves. It just starts with listening generously (see Step 1) and finding the problems that people are trying to solve, that no one is yet solving. How will WordPress' core vision, values, and mission help confront those challenges?

Until Matt's war against his own creation's fans ends, we will never know. But history shows that most Founders don't relinquish their control, and unless outside forces (investors, ecosystem magnates, significant partners, etc.) compel them to, they are more likely to bring down their creation rather than stomach the possibility that they actually, finally have to let go in order to see it become what they could never envision.