America's 'Simon Sinek' Problem

The ratcheting up of extreme expectations and what it reaps

The world’s leading leadership guru has a new company - The Optimism Company. And it should concern us for who it leaves out, how it raises the bar on interpersonal skills to elitist new heights, and what it distracts us from.

Simon Sinek, if you have not heard of him, exploded onto the leadership industry scene in 2009 when a Seattle TEDx¹ talk went viral in the true sense of the word, meaning no paid promotion was involved. It spread fast via digital ‘word of mouth.’ Ironically, the live audience at this event was tiny (100-200) compared to a modern TED talk (several thousand).

I encourage you to watch his breakout speech before reading onward. Hint: the fact that it is a verbal performance matters a lot.

You just listened to a naturally gifted presenter, possessing a rare charism. Almost none of us are this good, even with an outline and extensive rehearsal. Some of us could get there eventually, with hundreds or thousands of hours of practice and tough feedback swallowed with a smile. Most of us could never be this good. Ever.

Sinek makes it look easy because, for him, it IS easier. For the rest of us, especially those with verbal tics like me (e.g., tongue clicking, mumbling, tonal drops, etc.), it’s excruciating to meet this standard. Probably impossible. I may have done it only once or twice.

I’ll return to the interpersonal skills of today’s most admired business leaders in a bit, but first I need to dive into Sinek’s historical commentary on why some companies are wildly more innovative than others.

In Sinek’s viral 2009 talk, he shares what has now become a truism in American business - highly successful brands sell a movement or values system, not products or features or even just ‘outcomes.’ This, in part, is what drove the rapid growth of Whole Foods Market in the 2000s and 2010s—pitching a food movement, a massive cause. It’s the modus operandi of brands like Patagonia, Apple and Tesla in their respective heydays.

It is not a coincidence that the baby boomers’ takeover of corporate boards and C-suites coincided with the rise of a leadership guru named Simon Sinek. As this generation took over control of consumer-facing brands, those among them who had had the ‘social change’ or ‘movement’ bug inside them since their youth in the 1960s, such as Steve Jobs, unconsciously transferred this into their organizations as the new face of marketing and corporate leadership.

Companies that exude a passionate, world-changing ‘why’ make direct competitors seem like soulless bean counters. These ‘visionary’ companies also excel at attracting young talent.

It’s not that those less compelling competitors are unsuccessful; it’s that they don't garner pop culture attention because they simply sell products or services, without offering anything more to their consumers OR their employees. And their work cultures are also different, because this mysterious visionary ‘why’ is often lacking. Their work cultures are utilitarian, average, and stable. Not necessarily bad, just not inspiring; not ‘cool’ in the classic Baby Boomer sense of that phrase (think the Fonz, not the post-modern, sexualized “vibe cool” of Megan Thee Stallion). [If you’re over 50, I’d advise not clicking on the second link.]

The other thing that Sinek’s theory of leadership points to is the corporate culture that attracts the most ambitious talent in today’s corporate world. They want to be part of a ‘movement’ and achieve the cultural status of being employable within such a company.

If you look at the companies that Simon refers to, you’ll notice that they tend to be high-growth companies with enormous ambitions. In their rapid growth phases, they lent cultural status to one’s resume. This is in part, because the media covers high-growth companies the most. It’s a sad feature of a poorly regulated capitalist economy. Employees from high-growth innovators can often command above-market salaries when they leave, due mainly to the ‘innovation’ halo of their employers’ brands. It’s not the worst career strategy I’ve heard of.

Here’s a walk-through of some examples of high-growth innovators with visionary, ‘Sinek’ style leaders…by decade:

• 2000s - Whole Foods, Amazon, Apple, Facebook, Google, Netflix

• 2010s - Airbnb, Uber, Tesla, SpaceX, YouTube, WeWork, Spotify

• 2020s - Spotify, Liquid Death, Open AI, NVIDIA

But are these high growth, media darling growth companies necessarily the companies the average person will enjoy working for, in reality? Are these companies with killer growth, compelling vision, AND great to work for?

Pitting Company Vision Against Great Work Culture

As Sinek matured and gained more prominence, his thematic emphasis shifted away from the power of vision to the power of leadership that builds thriving, happy workplaces.

These are NOT the same thing, behaviorally.

One way to see if we need a visionary company to provide a great place to work is for us to look into the most rigorous worker satisfaction ratings we have available for large companies. And the one most business people recognize is Fortune’s 100 Best Companies to Work For, published every year since 1998.

Do the high-growth, innovative companies with visionary leaders make these lists? Do they stay on them, if they do? Or is it possible that there is no correlation between big, hairy, audacious vision talk and employee satisfaction?

To be eligible for the Fortune 100 Best Companies to Work For list, employers must have 1,000 or more employees in the U.S. and cannot be a government agency. 1/10th of 1% of companies in the U.S. have this many employees.² Simon’s business and this essay, therefore, focus on a rare group of admittedly very successful companies (consider starting one and growing it to 1000 employees). ³

Fortune evaluates companies along 29 behavioral criteria under the buckets of : Leadership, Experience, Culture and Performance.⁴ While most of the Fortune 100 offer paid leave benefits beyond what is guaranteed by FLMA, some do not. The evaluation is directly performed with employees. Management does not get involved.

Hilton is the number one company on their lists for the last few years. Here is how much ‘better’ Hilton is compared to the average US-based company.

The popularity of Fortune’s annual list with corporate management and Wall Street rests in their analysis of stock performance and its correlation to positive work culture environments. Board members have fallen in love with the idea of a great place to work for. They seem to like it far more than being a visionary innovator. And the data you see below is a major reason for their infatuation with ‘great workplaces.’

The implication is that large companies with high employee trust (peer-to-peer and peer-to-manager) offer a substantial productivity advantage. Increased productivity is what tends to make large companies more profitable over time, not rapid growth. Rapid growth usually requires spending net profits (and more) on more growth. Moreover, there are very. very few high-growth multi-billion-dollar revenue companies with more than 1,000 employees, despite the constant media appearances of a few like Nvidia, Amazon, and Apple during their respective heydays.⁵

But there’s another thing that high growthm innovative companies tend to do very poorly: train and develop their talent. They don’t have time to do this. It’s often managed chaos, one highly suited to narcissistic CEO-guru visionary types full of Sinek ‘why.’

In fact, institutional sociology since Emil Durkheim would basically predict this without any data. Many large, private institutions begin as small, guru-led movements. The ones that thrive transition into well-led bureaucracies without the paralysis the latter word implies. And they do not simply become scaled-up cults like WeWork became before it imploded due to its own incompetence and lack of ethics.

The Best Places to Work For Are Not Necessarily Led by CEO-Gurus

To explore the questions I posed earlier, let’s look at another list. Here are some of the companies that appear in Fortune’s Best Companies to Work For List every single year!⁶

• Wegman’s Food Markets (northeastern grocery chain)

• American Express

• Marriott Hotels

• Edward Jones Financial

• Intuit (think TurboTax)

• Salesforce

• Deloitte (management consulting)

• Carmax

• Publix (southern grocery chain)

• Adobe

• Scripps (San Diego-based healthcare clinics)

I could not afford to hire a computer programmer to produce an exhaustive list, but this seems like a relatively small proportion of the companies that have made the list annually since 2010.

Some of these companies are well loved and routinely covered in the media (e.g. Intuit, Adobe, and Salesforce). But a lot of these companies are not ‘cool’ and do not have guru-like Steve Jobs leaders. I mean, do you know the CEOs of any of the companies I just listed?

OK. Now let’s go back to my list from earlier. You know, the list of super innovative, high-ambition, guru-led companies. I crossed out the ones that have NEVER been on Fortune’s lists…ever.⁷

• 2000s - Whole Foods, Amazon, Apple, Google, Netflix

• 2010s - Airbnb, Uber, Tesla, SpaceX, YouTube, WeWork, Spotify

• 2020s - Spotify, Liquid Death, Open AI, NVIDIA

Well, that’s awfully revealing, even for a qualitative analysis. Remember, I made this list BEFORE analyzing the Fortune 100 lists from 2010-2025. If you doubt my analysis, here’s an independent list of 2010 innovators we can also cross-check for status as Great Places To Work For.

None of these companies are on the Fortune 100 lists. None. The absence of so many, well-advertised, often guru-led visionary innovators does not mean working there is like a Soviet Gulag. But still. Makes you wonder.

Is there a fundamental tension between visionary high growth businesses and the broader definition workers have of a great place to work for (which seems to focus on treating them respectfully and caring about them as individuals).

Whether Visionary or High-Trust, You Won’t Be Working At Them

Only 15M adults work in the large corporations that Fortune surveys every year. That’s only 12% of the working population. Honestly, it’s a larger number than I guessed before using BLS data to confirm it. Still, 88% of us work at small or medium sized organizations. And most of the latter really work in small businesses, including me. [Note: don’t become self-employed, if you do not trust yourself!]

So, the struggle to work at a visionary innovator, a “great place to work for” or both is really a problem for a rare group of post-grads in America. Most of us will probably never find this kind of company willing to hire us.

This raises the question of who Simon Sinek’s addressable market really is?

Here’s the “why” behind Sinek’s Optimism Company -

We imagine a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are, and end the day fulfilled by the work they do.

Sinek’s optimism is clearly tied to his company’s revenue growth ambitions. He is going for the masses, most of whom work in not very profitable, low-growth, small businesses without a lot of resources for training. And the work may honestly be pretty dull. I’m sure Sinek sees his books and online offerings as the solution for this horde of businesses where most of us work. They will not have huge HR departments developing customized professional development processes.

In one sense, Sinek has codified the rules by which you create a super-elite company with highly competitive, engaged employees. A few of them are my business clients.

But, most of us will never work at this kind of company. In fact, the lines formed for every open position at these kinds of ambitious innovators and great places to work for is often so long, these elite companies can afford to be extremely picky.

They can easily filter out anyone with pink flags, let alone those withg red flags, during the interview process.

That’s fantastic for them, honestly.

But none of this ‘great place to work for’ elitism helps the average employee or ever will.

I was trapped in a company I could not stand for 15 years before I had a way out. And that exit required taking the psychological and financial risk of becoming self-employed. I did not have a resume that maded me employable at the kind of companies I’ve been discussing. Not at all.

So, I chose, out of necessity, working for myself. I gave up trying to find a great place to work for and made my own.

Is Simon Sinek Just Codifying A New White Collar Elitism?

Obviously, I believe he is. And it’s not realistic for millions of us to latch on to the dream he sells.

Sinek claims to want to make companies super-engaged and well-led, yet the standard he sets depends on rare personal gifts from company leaders, tons of coaching, lots of high-trust leaders and also excess staffing that permits things like paid maternity leave, bereavement leave, etc. I only have one fast-growing client who set his company up to be like this - Once Upon A Farm.⁸

In fact, a lot of the traits Fortune evaluates are expensive to offer and administer. Professional development is not cheap. It requires internal and external resources AND it requires overstaffing so that each employee has time (not overtime) to take advantage of these resources.

Small businesses and startups simply can’t be this generous and communally supportive to their employees. There’s just no way. The local Teriyaki or Boba shop can’t offer these elite employee benefits either. They’re just trying to survive.

The sad reality is that Simon even has an audience at all. Because, a lot of what makes a company Great To Work For should be paid for and guaranteed by federal law.

Instead, companies get to compete with each other by offering a better workplace environment, thus excluding the majority of workers by definition.

This makes me sick to my stomach, because it’s so American.

Social progress becomes reduced to a private sector competition that yields progress only for an elite few.

I’m so tired of this. And it contributes to the sense of abandonment and grievance among MAGA extremists as well. I’m willing to bet that you won’t find hard core MAGA supporters at all among the Great Places to Work For.

We let our country turn into this bifurcated reality.

1. TEDx is a brand associated with the TED Conference, held annually in Vancouver. Local professionals can organize a TEDx event, receive training from the TED organization to meet its standards, and provide speaking opportunities for local experts to share their work and popularize their ideas.

2. https://www.naics.com/business-lists/counts-by-company-size/

3. The list includes public and private companies, presumably absorbing most of the ‘unicorns’ prior to their IPOs as public firms later on.

4. Here is their full methodology statement “

Our Methodology for:

Fortune 100 Best Companies to Work For® 2025

Great Place To Work® has been surveying employees around the world about their workplace experiences for 30 years. We have developed a set of themes and metrics that not only predict whether employees feel their workplace is great, but predict retention, agility, and overall business success.  

Using our proprietary Trust Index™ survey, we measure the core of what we know creates great workplaces — key behaviors that drive trust in management, connection with colleagues, and loyalty to the company.  

The survey enables employees to share confidential quantitative and qualitative feedback about their organization’s culture by responding to 60 statements on a five-point scale and answering two open-ended questions.

Employees tell us whether leaders are accessible, communicate honestly and clearly, and if their actions match their words. They tell us whether they feel respected as individuals, if they receive training benefits, appreciation, support for their well-being and opportunities to contribute. They tell us whether they believe their company is fair related to pay, profits, promotions, recognition, favoritism and opportunities. They tell us if they are proud of their work, their team, and their company and if they feel they make a difference, and their work is meaningful. And they tell us whether they enjoy the people they work with, feel cared for and can be themselves.  

List rankings are based on this employee feedback, which we analyze to determine the extent to which this experience is shared by the full workforce. Great Place To Work measures the differences in survey responses across demographic groups and roles within each organization to assess both the quality and consistency of the employee experience. Statements are weighted according to their relevance in describing the most important aspects of an equitable workplace. 

Companies with the broadest sets of employees who report positive workplace experiences receive the highest rankings on lists.

In addition to analyzing employee feedback for the Fortune 100 Best Companies to Work For® list we also consider what a company can tell us about their programs and workplace strategy. Each company also answers six essay questions that provide greater insight into how, and why the organization is great for all people. Responses are rigorously evaluated and cross-reviewed according to Great Place To Work’s research-driven criteria. From what companies share in datapoints and essays, we identify the organizations that offer the most generous, caring and innovative programs reflecting a genuine commitment to meet their people’s needs inside and outside the workplace as validated by what employees themselves report in survey results.

Surveys must meet strict requirements for how they are distributed and the percentage of employees who respond to ensure they accurately represent honest feedback from the company’s full population. While essay responses provide important context for rankings, only survey data can garner a list placement. To be eligible for the Fortune 100 Best Companies to Work For list, employers must have 1,000 or more employees in the U.S. and cannot be a government agency. In the last year, Great Place To Work surveyed companies employing more than 8.4 million people in the US and received more than 1.3 million responses. Of those, over 670,000 responses were received from employees at companies who were eligible for the 2025 100 Best and this list is based on their feedback.”

5. Note that the media love to label a company a ‘billion-dollar’ unicorn by using valuation or market capitalization as the metric, when almost none of these companies produce a billion or more in annual recurring revenue. America has approximately 1,500 billion-dollar revenue-generating companies. Source: https://companiesmarketcap.com/

6. This is not a comprehensive list, but it has most of them after checking a 30-40 of the companies that appear in multiple years. I could not get AI or Excel programmed to do a perfect analysis.

7. It’s possible that a few of these large corps refused to participate in Fortune’s survey process…but this itself would be an odd posture in a competitive labor market, certainly an arrogant one.

8. OFARM was #64 on Fortune’s 100 Best Small Companies to Work For (2024).