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Yes, billionaire operators have imposter syndrome, too
Debunking the myth that unicorn operators don’t feel imposter syndrome, and how to work past it
Regina Gerbeaux
March 02, 2025 • Reading Time: 19 minutes
Hi friend,
Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.
Preface
At least once a week, imposter syndrome comes up in my coaching sessions. That includes sessions with extremely accomplished, wealthy, and famous operators.
Sometimes, it comes up as an explicit conversation:
“I feel like an imposter, like I’ve somehow tricked all of my investors into giving me money, and deceived my team into leaving their high-paying, secure jobs to come work with me.”
Other times, it’s a little more discreet:
"I know I should be able to handle this, but sometimes I wonder if I'm really qualified to be making these kinds of decisions. What if I'm not cut out for this?"
So though I am aware that the topic “imposter syndrome” has been written about to death (Google currently has over 70 million search results!), I want to use today’s Issue of Force Multipliers to write about imposter syndrome from a billionaire operator’s perspective, and what to do about it.
Let’s dive in.
The Billionaires with Imposter Syndrome
A story I often think about comes from one of my earliest days as a Chief of Staff.
I was sitting in on a coaching call with an extremely successful operator whose company was then worth well north of $5B (a lot more now - but I digress).
I wondered: Why does this person need a coach? What more is there to prove? Surely, someone with such immense wealth and success feels completely secure in themselves, right?
I expected the conversation to revolve around revenue and strategy - perhaps discussing launching a new product line or making key hiring decisions to support explosive growth.
But I was wrong.
Two hours passed, and the company was never mentioned once. Instead, the entire session was dedicated to a different area entirely - the operator’s love life.
Dumbfounded, I listened as this billionaire founder lamented that the person they loved wouldn’t even go on a date with them. In their mind, it had to be because they hadn’t made “enough” money yet, that their company wasn’t successful enough.
I remember thinking: “Do you really think it’s because of money? You’re like a gazillionaire!”
Today, I’m not shocked at all. Nearly every ultra-rich, successful operator and leader I’ve met has, at one point, felt this way.
Some feel like imposters when it comes to money; others doubt their leadership abilities; still others worry about their capacity to command a room.
So, if you feel imposter syndrome - if you’re wrestling with self-doubt or insecurity - you’re in the company of many ultra-wealthy people. And it’s not inherently problematic. While you can’t control the initial surge of fear, you can control how you respond to it.
Let’s get into the question of the week.
Issue No. 2: Yes, billionaire operators have imposter syndrome, too
Dear Regina,
I am a Chief of Staff that recently got promoted to Head of Operations. I am excited for my new role and responsibilities, and I’m one step closer to becoming a COO, which has always been my career dream.
But I feel like everyone on the team perceives me as being junior and inexperienced. I’ve heard that my reputation is, “Very good operator, and excellent at her job, but too nice. Can she make hard decisions, or will she get steamrolled by the leadership team and just go with whatever it is they want?”
And I still live in the shadow of my exec: it’s hard shedding the role as “so-and-so’s Chief of Staff” after being that for almost two years.
All of this, compounded with the fact that our company is a unicorn worth $2B, makes me question whether I’m really capable of being Head of Operations.
How do I shift out of this mindset so I can truly do a good job?
Head of Operations, Series C company, ~70 people, $2B
Dear Operator,
Let’s begin with a reflection of what imposter syndrome is: an unresolved fear.
There is always a fundamental fear our brains like to tell us when we feel imposter syndrome: inevitably, it shows up in one or more places in your role in which you feel less confident than other areas.
This is why imposter syndrome is so confusing: on one hand, you might know that you’re world-class at Class A of skillsets, but you might feel a little more shaky at Class B, and you might know next to nothing about Class C.
For example: say you’re an operator like the one who wrote in above. You have always done well with interpersonal skills: you are high EQ, know how to read a room, and can accurately predict how people are feeling and what they’re thinking - you know you’re good at these things with maximal confidence. You love helping your exec and reading the rooms for them, especially because you’re aligned with them 95% of the time.
However … what happens when the 5% shows up? What happens if you have to have direct, hard conversations with people that will make them experience unpleasant feelings? What if you have to challenge your exec and tell them they’re wrong, or that they are about to do something they will regret? What then?
This is where imposter syndrome might creep in for you: the fear narrative is, “I don’t have enough trust with my execs to tell them with confidence that they’re wrong - I feel fear that they will react negatively to the information I’m about to tell them.”
Where is my imposter syndrome?
Here’s a tip on how to spot your imposter syndrome that works every time: look at your strengths. What is in your Zone of Genius? Every Zone of Genius has a potential drawback. Here’s a list of ones that might resonate with you:
Extremely in-tune with peoples’ emotions and mental states | Worried about having difficult conversations courageously |
Great attention to detail and organizing information | Takes too long to get work done; almost always underestimates how much time you’ll need to finish something |
Very outspoken and opinionated | Unapproachable and conjures fear when people disagree with you |
Excellent at the hard skills of the job (e.g.: forecasting, hiring) | Terrible at the soft skills of the job (e.g.: 1-1s, career mentorship) |
Great at getting in the weeds for the day-to-day execution | Taking the 10,000 ft view to think more strategically |
Methodical decision-making | Terrible at gut decision-making or making seemingly more impulsive decisions without full information collecting |
Every operator struggles with one or more of these places. And of course, you can take the above list and reverse it: maybe you’re great at gut decision-making, but have less patience for methodical decision-making.
This also applies to areas outside of your work life. Any time you feel insecure about something, take inventory of what is actually causing the imposter syndrome to creep in.
What’s the story, Gertrude?
So! Now you know what your fears are. Ask yourself:
What is the story I’m telling myself here?
Notice we’re using the word “story.” Plenty has been written about this already by Byron Katie, Diana Chapman, and many other conscious coaches, but here’s the principle:
If you recognize that your brain is simply telling a story based on the fear, you can know that stories aren’t always true. Therefore, your fear might not be true.
Want to know why this section is called, What’s the story, Gertrude? Because Gertrude is the name I’ve given our invasive fear-based thoughts that pop up in our minds all day long. One of the most powerful moments in coaching is when an operator discovers that just because they have a thought, doesn’t necessarily make it true. (For further reading, I recommend checking out The Untethered Soul, by Michael A. Singer.)
When you ask yourself what your fear story is, allow yourself to run wild.
Remember the operator’s fear above? Here it is again:
“I don’t have enough trust with my execs to tell them with confidence that they’re wrong - I feel fear that they will react negatively to the information I’m about to tell them.”
The wild, Gertrude-version of this story is:
“If I tell my exec they’re wrong, they’re going to lash out and tell me that I’m the one that’s wrong, not them. They are usually reasonable people, but this is an area where they have a hard time admitting they know less. They’re also such a gut-based decision maker, and this isn’t one of those areas where we can afford to have a mistake because of their gut.
They’re going to think I’m an idiot. Then, I’ll lose credibility and trust with them. Because they’re the CEO, the rest of the leadership team will sense the CEO doesn’t trust me as much anymore, so they also will think I’m an idiot. They won’t actually say I’m an idiot, but they’ll think it.
And then eventually, if I am wrong in my decision, and their gut is right, they’ll question whether I’m a good operator at all. What if I’m not a good operator? Then no one will ever want to work with me ever again. And I’ll never be COO, not here, not anywhere.”
Okay, holy shit - you just went from 0 to 60 mph in 3 seconds! But do you see how quickly our brains can trick us into telling these whole, elaborate stories based on a single thought?
From that story, you can ask yourself: what does this story tell me about me and my character?
For example, if it started as, “I want to be cautious about how I approach this conversation with my exec,” it can morph into, “I am scared I am fundamentally bad at having sensitive conversations and winning people to my side of the argument.”
What if Gertrude was…wrong?
Gertrude is almost always wrong. Your fear is almost always, at worst, an exaggerated version of the truth, and at best - just flat out wrong.
Now, you can ask yourself: What would your life look like if you didn’t believe this about yourself?
A lot of junior operators I meet have fears around hard skills: what if I suck at financial forecasting? What if I don’t know how to do a proper read on a P&L statement? What if I’ve never set up a complicated tax structure? (The character story here is: I must be an incapable, inexperienced operator. I’ll never be a real C-Suite leader.)
On the other hand, a lot of senior operators I meet have fears around soft skills: what if I come across as unapproachable? What if I’m seen as too much of a hard ass? What if I am too hard on my team? (The character story here is: I’m not the CEO at the end of the day, and I’ll always be #2 at highest in the leadership team. That must mean I will never have real decision-making power and influence. I will always live in the shadow of the CEO.)
Remember how you identified what the story said about your character? What if you didn’t believe that about yourself? What would your life be like?
I imagine you’d feel relief. You’d take a sober look at your strengths and weaknesses, and figure out how to lean into your strengths while bringing your weaknesses up to an acceptable level.
But you would NOT see your weaknesses as reflections of your character’s deficiency. A lot of times, I have to remind the operators I coach that discomfort doesn’t represent inadequacy or mean you’re an imposter; discomfort signifies growth.
💡 So write it out: what would your life look like if your fear was actually wrong? What if it wasn’t a reflection of your character - what if we could look at it more logically and objectively?
Mario Kart, and what an operator actually needs
Have you ever played Mario Kart? When I was younger and tried to build my kart, I would get frustrated: why can’t I have great drift and great braking and great speed and great handling? I want ALL of the best!
But that’s just not possible. Every kart is built on trade offs. You can get as close as possible to building the ideal kart for you and the way you typically drive, but you can’t ever have max OP skills on everything.
Like Mario Kart, your ideal skill set will be different compared to that of another operator’s.
Every company needs something different: a startup in heavy regulatory spaces will need different skills compared to a startup in well-defined, less regulated (non-life or death) spaces. A small, nimble startup will need different operator skills compared to a large corporation. A huge company will need a different operator than a small one. And so on.
Stay away from comparing yourself to your peers. Focus instead on your situation and your company: what is it that your company needs of you? How can you turn this into motivation to succeed?
And finally, remember: humans are multi-faceted people. Is it possible that there is one in you that is capable of doing the things you need to do, like an alter ego? For example, if you’re more conflict-avoidant, can you nurture the version of you that speaks up? Or, if you’re more conflict-driven, can you nurture the version of you that opts to listen curiously rather than jumping to conclusions?
Nurturing the different skill sets you want to grow in, without worrying about what it says about you or your character, is the ultimate antidote to imposter syndrome.
Give me Actions, Regina!
(The Imposter Syndrome Antidote playbook)
Here’s a summary of steps you can take to combat your imposter syndrome (or feelings of self-doubt and insecurity):
Self-assessment
Begin by honestly reviewing your skills and competencies relevant to your operator role (or any facet of your life: more on that below.)
Rate yourself from one to five on how proficient you feel in each area. Focus on addressing lower scores to enhance your skills and confidence.
Challenge personal narratives
Examine the stories you tell about yourself. If you believe others perceive you as too junior or incapable, confront and address these assumptions openly.
Discussing and countering these stereotypes through self-awareness and assertiveness can significantly alter how you’re perceived.
Commit to growth
Recognize that discomfort can signal growth. Nurturing a mindset of resilience in the face of challenges enhances both skill development and personal strength.
Recognizing that discomfort is actually growth will help you run towards it - not away from it.
Demonstrate competence and build trust
Show through actions that you CAN rise to the challenges of your role! Take on difficult tasks or responsibilities demonstrating your capacity for leadership. This can help to dispel any misconceptions others might have about your abilities.
Each of the operators I coach have to work through this almost without fail every coaching session. It’s a natural part of life for those who are daring enough to want to grow and become very successful.
And as a last suggestion: I want to encourage you to take inventory of your entire life, both inside and out of work. Where else do you feel a lacking, or self-doubt? Do you believe one day, your partner or best friend will wise up and realize you’re a shitty human being, and they’ll leave? Do you think that your community would leave you if they really knew your deepest, darkest secret? Do you struggle on doing things like managing your household finances, looking at all the bills to invest wisely, or other money-related matters?
Imposter syndrome lives everywhere. Use these steps to identify where they are, so you can stamp them out one at a time. I guarantee, your life will become measurably better without Gertrude following you around all day, telling you you’re not good enough.
Conclusion
Going back to the story of the billionaire operator from the beginning: I would like to think if they applied this Playbook to their dating life, this is what they would discover:
Self assessment: I am an excellent company builder and operator. I am a visionary and that has led to me building one of the most famous, successful unicorns in Silicon Valley today.
I am shit when it comes to my love life and, in general, understanding people. I am in love with this person, and they do not feel the same; they won’t even go on a date with me.
Personal narrative: The story I tell myself is I must not be making enough money. I always believed, since childhood, that if I was rich and successful, I could have anyone I wanted. My mom always told me to put my head down, work hard, and be successful: then, I could have my pick of romantic partners and friends, and everyone would like me and want to be around me.
Therefore, the reason I’m getting rejected must be because I’m not rich and successful enough.
Growth: When I step back and objectively look at my life from the perspective of “skill sets,” I am plenty rich and successful. There aren’t that many people wealthier than me. So it’s probably not a rich and successful problem, though the younger version of me wants to painfully believe this.
In reality, I’m just bad at reading people. This person won’t go on a date with me, because I’m not very good at being attentive or responding to their texts in a timely manner. They also don’t really care much about money: they see it as a means to an end, rather than something to collect and hoard. It’s so different from my perspective, so it’s hard to believe, but I know it’s true.
Building competence and trust: I should probably start by returning text messages to people I care about in a more timely manner. And maybe I’ve spent enough time chasing personal wealth, that I can allocate more time towards developing my personal life: I really want a family someday, and this would be something I should probably prioritize right now at my stage and age of life.
I should also go say sorry and really mean it to this other person. They might not like me back, but I have definitely acted below the line and gotten upset and angry when they rejected me. This would be a good first step in growing in my interpersonal skills.
Imposter syndrome, often misunderstood, is not a unique affliction of the unqualified or inexperienced. Rather, it is a shared human experience. The good news is, engaging in self-reflection, actively challenging limiting beliefs, and confronting fears will give you the steps you need towards overcoming feelings of inadequacy.
Ultimately, it is essential to recognize that growth often arises from discomfort and that reaching out for support through coaching and shared experiences can significantly bolster one’s confidence and capability.
Hope you liked this one today: what do you think? Do you want more stories of billionaire operators and the kinds of problems they deal with? Let me know.
I look forward to you joining me in Issue 3 of Force Multipliers! Next time, we’ll talk about the most pressing and highly requested topic: how to manage difficult personalities on your executive leadership team.
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About Regina Gerbeaux
 | Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale). Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz. |
Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.
She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.
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