Jack Dorsey and Twitter: A radically different take on a founder’s story
Every piece of commentary you’ll find on Jack Dorsey refers to him either as Twitter’s founder or its (now former) CEO. Yet he holds a less understood but far more important third role which give us a radically different story of what’s going on with his transition ‘out’ of Twitter.
This article offers a brief introduction to this different perspective, then we can look at what’s happening with Jack and Twitter through a new lens to uncover some radical new insights, questions and risks being opened up by the process.
Why this matters
All transitions where a founder-CEO leaves an initiative carry great risks of a predictable set of problematic scenarios:
- a drift to extreme leadership following the transition in either an overly authoritarian, or the opposite: a weak, watered down style
- a meddling founder who’s really still in charge even without a formally recognised role, causing confusion and power struggles
- a restless founder driven to distraction by the mounting problems they observe in the endeavour they started and unable to focus on the next chapter of their life
- the emergence of an unofficial channel of authority from the outgoing founder to the initiative, via a representative
- a focus on money, not vision, sapping the creative vitality from the endeavour, and, paradoxically, financial peril over the longer term
These problems can be the undoing of all the great work a founder did, and also prevent them from fully moving on to whatever they wish to do next. I’ll explain them in more detail later in the article.
This is not only about Jack Dorsey and Twitter, but it applies to founders of all human initiatives: Companies, social movements, open source projects, cryptocurrencies and artistic productions. In fact all attempts that humans make to bring something new into the world.
I’ve never met Jack, but I think that in so many ways he embodies much of the hope I have for creative upstarts that goes far deeper than the tired old Silicon Valley mythology around founders. I hope serendipity brings this article into his awareness and perhaps brings some risks and possibilities out of blindspots and into view.
A powerful new perspective on being a founder
Being a ‘founder’ is a role based on a historical fact that someone like Jack Dorsey started an endeavour. Meanwhile, being a ‘CEO’ is a formal job title and set of expectations based on the norms and mindsets of the corporate world. But let’s look at Jack’s role in a third way.
To do this, we need drop the focus of our attention down a level deeper than corporate constructs like shareholdings, boards and official job titles. As we do this, we can ease off the story of Twitter primarily being a corporate entity, like it’s a separate “thing” with an existence of its own.
As we shift our gaze, we can instead look at Twitter not as an entity, but as a creative process; a story which began to unfold from the moment Jack first invested himself in his nascent idea, and continues to this day.
From this alternative perspective, we see Dorsey not only as a founder and outgoing CEO, but in another role which my friend, the seminal thinker Peter Koenig called “the role of source”. By acknowledging Jack in this role, an entirely new perspective emerges.
I wrote a book all about this, but here’s a lightning fast primer of the basics.
The role of ‘source’
In every human initiative, you’ll find a single person in the role of ‘source’. It’s a naturally emerging role that comes into being when the first individual takes the first vulnerable step to invest themselves in the realisation of an idea. I’m pretty certain this is Jack’s role in the Twitter story, separately from any of the other original co-founders.
The role of source is not a formal position like a CEO. Think of it as an artist, the natural author of the story, the person whose job it is to listen carefully for where it is heading and find clarity over what needs to happen next. Like all artists, the source’s work is deeply connected to their individual sense of purpose and creativity.
This doesn’t mean the source is some omnipotent dictator or mythical “hero visionary entrepreneur”. A source such as Jack working on an idea like Twitter needs to foster the participation of many other people, and to do this they need to show up in the role in a certain way: less commander-in-chief (although that might be necessary on occasion) and more often, like chief listener. It’s actually a very vulnerable role, where the chronic condition is one of doubt about what must come next, and where much help and support will be needed to keep turning vision into reality.
The concept of the role of source can feel too mystical or spiritual for some people with a purist, rationalist bias. Meanwhile, for those with a highly egalitarian value system it can be hard to stomach the idea that one individual is in a special, naturally emerging role. My experience is that they usually come around eventually when they have personally experienced the dynamics around the role of source playing out in the initiatives they’re involved in, and they realise their old mental model is insufficient.
How authorship is shared
In corporate settings, we think of authority (note the root of the word being author) being shared through management hierarchy and explicit job roles, and often coming with a sense of power over people.
From the perspective of source, we see authority a different way: A source can share the authorship of the vision and get out of the way as others become specific sources for parts of the whole, taking on the exact same role of source within specific domains, as well as often contributing ideas that expand the vision in generative ways beyond that which the overall source could ever have imagined.
Far from being subservient to the source, specific sources are also living their own personal calling in life; they merely choose to express this some or all of this calling within someone else’s broader initiative. I’m certain this will be the case for many initiatives within the overall wrapper of what we call “Twitter”.
Succession of source
Finally, and most importantly, the role of source can be passed along a line of succession through many generations, always from one individual to another. The deepest values of the initiative are passed on, while the creative vision for what is being brought into the world evolves. So whilst it begins with a first founder, a source can be a successor who came on the scene later.
It’s critical to understand that all of this happens completely separately to formal elements of succession like handing over a CEO role, joining or leaving a board of directors, or making changes to legal ownership of a corporate entity.
So what does this new perspective tell us about Twitter and how the problematic scenarios I laid out could become manifest? Let’s dive in.
Jack Dorsey’s transition from a source perspective
Let’s start by looking at the key parts of Jack Dorsey’s letter to his Twitter colleagues. He wrote:
There’s a lot of talk about the importance of a company being “founder-led.” Ultimately I believe that’s severely limiting and a single point of failure. I’ve worked hard to ensure this company can break away from its founding and founders.
It’s absolutely true that it’s highly limiting to insist on a company being founder-led, not least because it would be limited in time to the life of the founder. Yet there’s more nuance to add to this.
There is a noble wish here for Jack to separate himself from Twitter. Yet I suggest that a deeper truth is that art is never truly separate from the artist. It’s an expression of them.
Perhaps unfortunately, this does mean there really is a single point of failure. It might not be something we’d wish to design deliberately into a system, yet countless examples of failed initiatives following a founder leaving suggest we ignore this at our peril. In our research into the role of source we see failure when there’s an attempt to deny the individual nature of the role of source and spread it around more than one person, or for a source to leave their endeavour without passing on the role.
Companies are not like children of their founders. They are not sentient beings that can enter an adult phase of life free from the oversight of their “parents”. If we let go of the story of companies being “entities” at all (other than for corporate, administrative purposes) and instead look at them as unfolding stories, it becomes clear how they can only continue if they have an author writing the story.
But Jack is right that this doesn’t have to be an original founder. If the role of source is passed on successfully then the founder can indeed fully transition away and the story can continue, full of life, under the watch of a successor.
The question is, has the role of source truly been passed on?
The board ran a rigorous process considering all options and unanimously appointed [new CEO] Parag [Agrawal]. He’s been my choice for some time given how deeply he understands the company and its needs.
So has there been a succession only at the corporate level of board member and CEO, or at the deeper, creative level of the role of source? Has Jack truly let go of his role as the artist who is writing the Twitter story?
It’s possible to have a full transition around job role, directorship and shareholding without a succession of the role of source. From a corporate perspective, a CEO is accountable to the rest of the board (acting on behalf of the shareholders), yet from the deeper, creative perspective we are taking here, the source is the ultimate authority and that persists indefinitely, even if they resign or are fired from their formal role. So what’s happening with Twitter?
One interesting signal is that Parag was apparently Jack’s clear choice. This is essential for a succession of source. The process happens naturally between two open and willing participants — one letting go and the other receiving. It cannot be forced. Not by a corporate board, the law, or money.
My colleagues and I have witnessed and collected many accounts of processes of succession of source, and when it happens it’s unmistakable. Both the outgoing and incoming source remember a specific moment when the succession happened. They often speak of something they can only describe as an “energetic shift” as the metaphorical baton is passed. If that deeply moving, memorable moment hasn’t clearly happened, we can assume that the role of source has not been passed on yet.
Dorsey continues about his successor, Parag:
He’s curious, probing, rational, creative, demanding, self-aware, and humble. He leads with heart and soul, and is someone I learn from daily. My trust in him as our CEO is bone deep.
If there is deep trust from Jack, then a succession of source is possible. And if Jack’s assessment of Parag is true, this is a promising set of attributes. Most importantly, expressing creativity, heart and soul will be vital for Parag as a source. Remember, it’s first and foremost an artistic role, not a formal leadership role.
Jack also said that Parag “understands the company and its needs”. If we let go of the notion of Twitter being a separate entity which can have “needs”, we can acknowledge that Jack as the source of Twitter is the one with needs. What was the whole endeavour really about for him? Is he truly complete and ready to let it go? If there’s anything he’s still really hanging on to then a succession of source won’t happen.
The second [reason for the timing of my departure] is Bret Taylor agreeing to become our board chair, I asked Bret to join our board when I became CEO, and he’s been excellent in every way […] Having Bret in this leadership role gives me a lot of confidence in the strength of our board going forward. You have no idea how happy this makes me!
This could be an interesting twist. Perhaps the real successor of source is Bret, not Parag. I wonder what Jack would say. It doesn’t matter what their official job titles are; the question is whether Bret or Parag will be the one who really takes on the holding of the Twitter story’s deepest sense of values, with the other taking on a more specific role of source for part of the endeavour.
My intuition is that that Taylor is there to shore up the coverage of more corporate responsibilities. He was invited in by Jack. So if there is a succession of source happening here, I would say it is to Parag. It will help all involved to be clear on this.
All of you have the potential to change the course of this company for the better. I believe this with all my heart!
This nod to the value of everyone involved in Twitter illustrates the potential for many others to acknowledge themselves as specific sources within the wider initiative, if the conditions are created by the source.
If Parag has indeed taken the role of source from Jack, then he’ll need to simultaneously adopt both a top down position of authorship over the outer edge of what Twitter is and is not, whilst also fostering a bottom up stance to allow specific sources to fully step into authorship for their parts of it. He must do this while also holding the tension all sources feel between doubt over what needs to happen, and the clarity that eventually comes to them alone. And further, he must also engage in the necessary “inner work” to integrate the many characters, or identities a source might have to show up as at different times along the way, and not project parts of his own psyche onto “the company”, other people, or money.
Doing this well is a real art, beyond what we typically think of as “leadership”.
Parag is CEO starting today. I’m going to serve on the board through my term (May-ish) to help Parag and Bret with the transition. And after that…I’ll leave the board. Why not stay or become chair? I believe it’s really important to give Parag the space he needs to lead. And back to my previous point, I believe it’s critical a company can stand on its own, free of its founder’s influence or direction.
The stated intention here is for a clean break, which would require a succession of source. But is it really true? How much of this departure is about pressure being applied by corporate shareholders unhappy about Twitter’s share price or Jack’s split attention between Twitter and his other company, Square? To what extent is Jack genuinely ready to move on? Only Jack himself will know the answer to that question, but it will have a huge impact. The succession cannot be forced, just like how signing marriage or divorce papers cannot make anyone genuinely fall in or out of love. These things operate on a deeper plane.
Jack says he’s staying on the formal board of Twitter the corporate entity until next May. If the succession of source hasn’t truly happened yet, perhaps this is a window of time when it can be consciously completed.
There aren’t many companies that get to this level. And there aren’t many founders that choose their company over their own ego. I know we’ll prove this was the right move.
Rampant egos are, of course, problematic. Yet we see time and again that a source does have a special, intimate relationship with the endeavour they are holding — there can be no real separation until the role of source is passed on, and that will a deciding factor as to whether this is looked back on in the future as a successful move.
If a source leaves their initiative and a creative succession hasn’t been completed, certain unhelpful dynamics are likely to play out. These dynamics often involve confusion and blame, but, by looking at the situation from the perspective of source, we can see what’s really going on and cut through any bad feelings that may have developed. It’s nobody’s fault; there was just a lack of awareness of what was happening at this deeper level of source.
Here’s a closer look at the five problematic scenarios I mentioned earlier, that point to an incomplete succession. We can all watch carefully for these happening at Twitter.
Scenario 1: A drift to extreme leadership
The symptoms of a new CEO trying to take charge when they are not the source are utterly predictable: At Twitter, be on the look-out for either a drift towards an overly authoritarian leadership style, as Parag attempts to exert control by force, often without natural consent from others, or a swing to the opposite extreme, with endless consensus seeking and the watering down of a creative vision for the endeavour.
In my work as an advisor, I’ve even seen situations where a company bounces back and forth between the two extremes for many years with a succession of CEOs, never addressing the role of source issue. Each time, the leader is blamed, and the root cause is not addressed. These problems cause good people to leave, and the focus on a clear, creative vision to which people naturally want to contribute is lost.
Scenario 2: The meddling founder
Sometimes an outgoing founder just can’t stop themselves from meddling after they’ve supposedly left. When this happens, it’s very likely that they haven’t passed on the role of source.
Watch out for a founder who says: “I’m handing over to the new CEO, but I’ll always be the founder and I’ll stay on to offer guidance to the new CEO as the journey continues.” That’s a sign they aren’t ready to pass on the role of source. Parag has already mentioned Jack’s “continuing mentorship” and they should be mindful about what’s really going on between them.
Even after a new CEO takes office, other colleagues may still look to the old founder when it comes to the deepest matters of vision, values, and high-level direction. The new CEO may struggle to find a place in the new order of things. The CEO may well give up and leave (or be fired), blaming themselves, or the old founder, for the confusion.
The new CEO may also defer to the founder on key decisions. That’s fine if both want that relationship, yet in many cases this is not made clear, and a power struggle unfolds.
Scenario 3: The restless founder
It’s fascinating to observe how persistent the role of source is. Even if a founder left the formal organisation many years previously, the role of source stays with them until a succession process is completed or they symbolically ‘close’ the initiative altogether.
An outgoing founder can find it difficult fully to invest themselves in new initiatives with the same creative vigour they used to have, or to switch off and enjoy a relaxing retirement. It’s as though a significant portion of their energy is still occupied by the initiative, even though they think they’ve left.
Sometimes a founder will watch from a distance as their initiative loses its way and finds itself in some of the other problematic scenarios. They can see what needs to happen more clearly than anyone else, yet they’re unsure about whether or how to intervene. They may not want to undermine its new leadership, but they cannot bear to see it fail.
Scenario 4: The emergence of a source representative
Sometimes, when the source has supposedly left but a succession hasn’t truly happened, somebody within the initiative will still be in close touch with them and acting as a conduit for their views, even if neither of them is fully aware this is what’s happening. They may just think they are old friends talking, or that the source is just providing friendly advice that any experienced advisor could offer. But really it’s a channel for the deepest sense of authorship of the story.
In Twitter’s case, I wonder about the role of co-founder Biz Stone. Has he had an unacknowledged role as the source’s representative? Or was he even the source of the endeavour itself? The FT reports:
Stone helped to build Twitter’s culture before he left in 2011, only to return in 2017, at a time when the company was stagnating. He was to guide the business back to “that energy, that feeling” of its origins, or as he put it at the time, “the job description includes being Biz Stone”. Though no longer officially at Twitter, Stone claims he continues to act as an “informal” adviser.
The source representative scenario is preferable to an initiative drifting without any input at all from the source, yet, without the source directly taking responsibility for their initiative, the link is severely weakened. The source is not in a position to really listen and tune into what needs to happen, and acting via another person slows things down and makes it possible for next steps to be misunderstood. Since the representative will not have the same natural, creative authority as the source, when the representative communicates next steps, it will be much more difficult to bring others along.
All of this means the representative’s job becomes stressful and exhausting. It may help for a while, but it’s not sustainable. The most powerful thing a representative can do is to recognise the dynamic which has emerged and do everything possible to persuade the source to acknowledge their natural role. The representative must help the source to understand they haven’t truly left, and that ultimately the problems occurring there are their responsibility. Then the source can make a decision either to fully step up to their responsibilities again or to complete a succession process and fully transition out. It may turn out the representative is the ideal candidate for a succession, and, with that process complete, the reliance on the previous source will end and the new source can directly hold the creative field themselves.
An outgoing source like Jack can also watch out for this dynamic. When he meets colleagues still working in the initiative, he can tune into the nature of the conversation. Is he really just providing a sounding board and offering advice from a neutral perspective, or is everyone kidding themselves, or is he really generating the ultimate clarity over the vision and high-level next steps?
Scenario 5: A focus on money, not vision
When a creative initiative is in full flow, with a source taking responsibility for the vision to be realised, the initiative attracts the resources it needs, including people and money, and has a feeling of vitality.
When an initiative becomes disconnected from a creative vision, a focus on money often becomes its substitute. This can work for a while, but the company will become less creative, and it will become harder for it to attract the resources it needs. The best, most creative people will leave to start new ventures or join other companies which have more life in them. These creative people are often replaced by individuals who are themselves following money, not a creative vision.
Perversely, over the long term, the focus on money can make a company more financially precarious. Some of the best examples of this are once-vibrant start-ups which have become large public companies; cases that Jack and Parag would do well to learn from. After the founder leaves, a new CEO tries to please Wall Street. Microsoft under Bill Gates’s successor as CEO, Steve Ballmer, appears to have been just like this. The company can dwindle, perhaps never to return to its former glory.
In Microsoft’s case, Bill Gates, who we can assume was the source all along, returned to Microsoft. Then he appointed a new CEO, Satya Nadella, to help him realise a creative vision once more. Now all the signs are that, finally, Gates has handed over not just formal responsibility but the deeper role of source for Microsoft, and the company has a new lease of life. Nadella has the hallmarks of an effective source. He is not trying to play the hero visionary but more humbly and gently, yet still firmly, holding the space for a new vision for the company to emerge.
Relating to Twitter, Wired Magazine reported:
For the past year and a half, Jack Dorsey almost certainly knew that his time was limited. “Activist shareholders,” notably at Elliott Management, decided Twitter would be ripe for giant gains once they got the finicky CEO out of the way and put someone in to boost financials in the short term.
Is this Twitter’s fate? Perhaps it’s still in Jack’s hands, even after letting go of the formal role of CEO.
From the information in the public domain we can only speculate about the truth of what’s really going on with Jack Dorsey and his transition at Twitter. We can see hints of the deeper, more heartfelt story in amongst the corporate storylines of CEOs and boards of directors.
As we’ve seen, the two key questions are:
- Whether Jack was genuinely ready and willing to let go of not only the CEO role, but the role of source of the endeavour — being the author of the Twitter story.
- Whether this deeper succession process has really happened, and if so, to whom? The key test is whether both Jack and his successor remember a clear, ‘energetic’ moment when they deeply felt the role being passed.
If there is not a clear yes to both questions then going back to what’s happening at the level of the role of source will be key to allowing everyone involved to move on successfully without the potentially severe problems I’ve laid out.
I wish Jack, Parag and everyone involved in Twitter the best of luck… and, of course, my DMs are open if anyone wants to chat.