Founder’s Syndrome Has Entered the Chat
This was actually one of the very first newsletters I ever drafted.
The original version had a little more venom in it. At the time, I was coming out of years spent alongside founders who had worked incredibly hard to build what they had and professed to genuinely care and want all the feedback, but yet still couldn’t hear what their people were saying. I found myself acting as a translator in both directions. Softening or explaining founder decisions for the teams while simultaneously trying to explain to founders what they weren’t hearing (or didn’t want to hear).
It was exhausting and frustrating, and it made me complicit in a system I was trying to break.
Almost two years of consultancy later, I have a lot more empathy for this pattern and a much clearer view of why it happens. The original working title of this newsletter was an ode to Taylor Swift: “You, you’re the problem, it’s you.” Now I realize that laying blame isn't constructive; clarifying the journey from hero to architect is a better use of my time.
What Holds Companies Back
I’m often asked what I see as a company’s biggest problem. The answer is almost always a founder-CEO who can’t get out of their own way. They throttle growth by becoming the company’s biggest bottleneck, unable to separate themselves from the brand and decision-making, incapable of empowering the A-list people they hired to do their jobs.
They built the business through taste, instinct, relationships, and relentless involvement. Over time, those same strengths begin to slow the company down when everything still routes through them.
In the nonprofit world this has a name, it’s called Founder’s Syndrome. In hospitality, it’s just another Tuesday.
Common Signs of Founder’s Syndrome
This doesn’t show up as one dramatic failure. It shows up in patterns that may feel reasonable in isolation but corrosive in aggregate.
Micromanagement disguised as “protecting the brand.”
Despite hiring great people, I’ve seen founders copy-edit Instagram captions, veto junior manager hires they barely know, or ask for a presentation on a decision that should be made at the director level.
Endless iteration → no decisions.
Decisions are made, then amended, then reversed, then reinvented. Teams don’t actually need more or clearer direction; they need the goalposts to stay where they are.
Vision in their head, disappointment in reality.
The founder can’t articulate what they want and then feels perpetually let down by what is delivered. Everyone is trying to “read the tea leaves,” which is never a reliable strategy for operational excellence.
Employee Whack-A-Mole (aka “The List”).
Because the founder cannot see themself as the common denominator, blame becomes rotational. This quarter, it’s HR’s fault. Next quarter, marketing. Then the GM. Employees will do anything to stay off “the list,” which creates paranoia and avoidance (not performance).
The Shiny Object Employee (Employee Whack-A-Mole’s counterpart).
Every six months someone new is christened as the Savior. Hopes skyrocket, then micromanagement follows, expectations become impossible, and eventually: “They’re not who I thought they were.” It’s a tragedy in three acts. On repeat.
Why This Happens
Most founders worry, consciously or not, that if they step back, the magic will disappear. And to a degree, that fear is earned. Their aesthetic, their palate, their network, and their relentless hustle did build the business.
And often, their identity is so fused with the company that loosening their grip feels like erasing themselves.
The problem is that the skills required to build a company are not the same ones required to scale it.When a founder’s identity becomes inseparable from the organization, every decision starts to feel existential. Control feels safer than trust, even when trust would serve the business better.
Founder’s Syndrome is not a moral failing. It is a developmental one.
And Yet…There IS a Way Out
These are the antidotes that I believe actually work.
Shrink the number of founder direct reports.
Every additional direct report increases the gravitational pull back into the weeds. A founder should have 2-3 strategic reports, not 9-12 operational ones.Clarify roles, responsibilities, and decision rights. And commit to them.
Not “draft them 17 times.” Set them, share them, live them. If you have a founder who tends to endlessly iterate, set a 6-month or 9-month date in advance to review and reassess.Create a forcing function for decision-making.
A cadence (weekly, biweekly) where decisions are made and then closed. If everything can be renegotiated at any time, nothing sticks. Sometimes I, as a consultant, am that cadence, and it works.Teach the organization how to operate without reading the founder’s mind.
A founder’s job is NOT to disappear; it’s to translate vision into systems, values, and processes that others can execute reliably. (Guess who can also help with this?)Shift from “What do I want?” to “What will allow this company to succeed without me in the room?”
This is the mental transformation that separates sustainable companies from cults of personality. For this I can recommend some incredible executive coaches.
How You Know Your Company Has Founder’s Syndrome
One sentence tells the whole story:
Someone on the team: “In my professional opinion, I don't think this is best for the business, but I know it’s what the founder would want.”
That is not alignment or loyalty. It is fear, learned helplessness, and a total breakdown in organizational decision logic.
For the COOs, HR, GMs, and senior leaders reading this and recognizing their own experience, I see you. These dynamics shape your reality too, even when you do not have the authority to change them alone.
From Hero to Architect
The goal is not to remove the founder. It is to evolve them. From being the source of the magic to becoming the steward of it.
Founder’s Syndrome isn’t the mark of a bad leader. On the contrary, it usually means you have a successful leader who hasn’t been supported through the next stage of growth (or even introduced to the idea).
The work to be done is about designing a company that can carry the founder’s vision without requiring their constant presence to function.
And if you are a founder reading this and it landed a little close to home, that is often the first sign that a shift is already starting. The transition from hero to architect is hard.
I should note, I love founders.
My entire career has been working for founder-CEOs. They are visionaries. They bet on themselves. They take risks when most people won’t. They bring the energy and conviction that pulls companies into existence in the first place.
It’s also why so many excellent people are willing to endure less-than-perfect conditions to build alongside them.
So, to the founders reading this: you’ve hired the best of the best. Now it’s time to trust them enough to let them show you what they’re capable of. And if you need help making that transition, hire me to help!
