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Audrey Nesbitt Interview: From Visionary to Bottleneck, the Hidden Risk Founders Face

Silicon Valley has long worshiped its founders, the visionary engineers who turn caffeine and code into billion-dollar ideas. But what happens when the same brilliance that builds a company starts to break it? Somewhere between the garage and the boardroom, many founders discover that leadership is not just another problem to solve but an identity crisis. Audrey Nesbitt has seen that reckoning up close. After years inside fintech, blockchain, and AI startups, she has watched gifted builders lose their companies not to competition but to themselves. Her new book, “Why You Shouldn’t Be the CEO (And Other Ways to Save Your Startup),” argues that innovation cannot compensate for a founder’s blind spots, and that the courage to step back may be the most underrated skill in tech. In this conversation, Nesbitt dismantles one of Silicon Valley’s oldest myths: that the person who starts the company should always run it. She explains why real leadership often begins the moment you realize it might not be you. Your book questions one of the startup world
Silicon Valley has long worshiped its founders, the visionary engineers who turn caffeine and code into billion-dollar ideas. But what happens when the same brilliance that builds a company starts to break it? Somewhere between the garage and the boardroom, many founders discover that leadership is not just another problem to solve but an identity crisis. Audrey Nesbitt has seen that reckoning up close. After years inside fintech, blockchain, and AI startups, she has watched gifted builders lose their companies not to competition but to themselves. Her new book, “Why You Shouldn’t Be the CEO (And Other Ways to Save Your Startup),” argues that innovation cannot compensate for a founder’s blind spots, and that the courage to step back may be the most underrated skill in tech. In this conversation, Nesbitt dismantles one of Silicon Valley’s oldest myths: that the person who starts the company should always run it. She explains why real leadership often begins the moment you realize it might not be you. Your book questions one of the startup world's oldest assumptions: that the person who starts a company should also run it. What made you want to challenge that uncomfortable truth? I kept seeing brilliant founders come up with powerful ideas and get early traction, only to lose momentum when it was time to scale. Not because the vision wasn’t strong, but because they struggled with leadership. The skills needed to inspire a team, manage investors, and navigate growth are completely different from the skills that get a product off the ground. After years of working with startups in fintech, blockchain, and AI, I saw the same story play out. Founders who loved solving complex problems but dreaded managing people. Builders who were brilliant with code but avoided sales meetings and strategy sessions. Many took on the CEO title because it felt expected or because they felt entitled to it. In some ways, they were. They started the company, after all. But that doesn’t always make them the best person for the role. Sometimes it’s ego that keeps them there, not alignment. I’ve also worked with founders who never wanted the CEO role. They knew where their strengths truly were and had no interest in pretending otherwise. One stayed focused on product and innovation while someone else led the company, and it scaled faster because of that clarity. Another told me later, “I wasn’t a good CEO.” He’s now a successful investor who learned where he creates the most value. The CEO role isn’t about being the smartest or most technical person in the room. It’s about leading people, building partnerships, and making hard business decisions. Those are entirely different muscles from building products. I wrote this book to challenge founders to ask themselves an uncomfortable question: Do you want to be CEO because you are the best person for it, or because your ego says you should be? And it’s not a question you ask once. You should ask it at every stage of growth. You might be the right CEO in the beginning and not at scale, or you might grow into the role later. The key is staying honest about where you add the most value. The best founders know leadership isn’t about holding a title. It’s about doing what’s right for the company and the vision you set out to build. You point out that nearly two-thirds of high-potential startups fail because of founder conflict, not poor products. Why is it so hard for founders to see when they’ve become part of the problem? That 65 percent figure comes from Harvard’s Noam Wasserman, who argues in The Founder’s Dilemma that conflict among founders is the root cause of failure for many promising startups. Founders struggle to see themselves as the problem because they are deeply invested in their identity as the builder or visionary. Admitting you may be the constraint feels like admitting defeat. They develop blind spots that protect their ego; rationalizing control as “quality,” framing micromanagement as “standards,” or blaming external factors instead of owning internal dysfunction. Conflict often hides under the guise of vision alignment or culture maintenance. It doesn’t feel like a fight; it feels like doing what needs doing. And far more than being a failure of character, it’s a failure of structure and feedback. Founders generally lack objective frameworks to evaluate their impact, and asking for help feels like a weakness. To be self-aware, founders need a shift in identity: care more about the company’s outcome than their own image. Hire people who’ll tell you the truth. Build feedback loops. And at every inflection point, ask: am I enabling growth or becoming a bottleneck? The right leader at the start isn’t always the one to take the company to scale, you write. How does a founder know when it’s time to hand over the reins or at least loosen their grip? Founders often romanticize the idea of being the eternal captain of the ship, but scaling a company is a brutal Darwinian process where ego is the first casualty. The truth is, most founders aren't wired for every phase of growth. Your scrappy, visionary hustle that bootstraps a startup from a garage to $10M in revenue can become a liability when you're pushing toward $100M or an IPO. The "right leader at the start" is usually a chaotic inventor; the scaler needs a disciplined operator who obsesses over processes, talent pipelines, and risk mitigation. Recognizing that a mismatch isn't a failure; it's self-awareness with emotional maturity. But brutal honesty: denial is epidemic, and plenty of founders cling on until the board (or investors) stages a velvet-gloved coup, like Travis Kalanick at Uber or Adam Neumann at WeWork. They don't "hand over the reins"; they're pried loose, often with a fat payout. The smartest founders don’t wait to be pushed. They bring in operators, hire a president or COO, and test what it feels like to let go of control before someone forces the issue. They treat succession as a strategy, not a punishment. Many technical founders take pride in their perfectionism and control. How do those same traits that helped them build their product end up holding the company back? Technical founders often fall in love with their perfectionism and that tight grip on every detail. It’s what gets them through those brutal early days of building something from nothing. Back then, it was a superpower. You tweak every line of code, every button, every feature until it not only works but feels right. That obsession pulls in your first users and gives the company its spark. But when the company starts to grow, that same instinct quietly turns against you. The habits that once saved the startup begin to slow it down. Take product launches, for example. You hold back for one more fix, one more polish, while a competitor ships something rough and gets real feedback. By the time you release your “perfect” version, they’ve already captured the audience and set the standard. Watching that happen hurts, especially when you know your product might have been better if it had just reached the market sooner. It shows up inside the company too. You start rewriting your team’s work, second-guessing decisions, and micromanaging because things aren’t exactly how you’d do them. The team loses momentum, good people leave, and decisions that once took hours now take weeks. The company that started as a nimble experiment becomes a slow-moving machine. It’s a cruel twist. The traits that built the foundation end up setting the limits. To scale, you have to let go a little, trade precision for perspective, and trust others to carry the vision forward. The founders who figure that out early are the ones whose companies actually make it past the growing pains. In the book, you outline tools like the Five-Point CEO Self-Assessment and The Three Phases of Founder Evolution. How can founders use these frameworks to stay self-aware as their companies grow? The Five-Point Self-Assessment forces founders to get brutally honest about five critical areas: the Energy Test (what drains you versus what energizes you), the Competence Test (where are you truly world-class), the Enjoyment Test (what does your ideal workday actually look like), the Five-Year Test (what do you want to be known for), and the Influence Test (do people follow you because of your vision or just because you're the boss). Most founders never ask themselves these questions until it's too late. They're so busy executing that they don't notice they've been miserable in the CEO role for two years. The framework works because it's not about whether you can do the job, it's about whether you should. There's a massive difference between capability and optimal fit. The real power of these frameworks is that they give founders permission to be honest with themselves without it feeling like failure. You can look at the assessment results and recognize that you're spending 60% of your time on activities that drain you, realize you're in the wrong phase for your company's size, and make strategic decisions about your role based on data rather than ego. The goal isn't to force yourself into the CEO role if it's not the right fit. The goal is to optimize for where you add the most value, whether that's as CEO, CTO, President or Chief Product Officer. Sometimes the best leadership decision is recognizing when someone else should be leading. You’ve led teams across fast-paced, high-pressure industries, including fintech, blockchain and AI. Do these sectors create different leadership challenges than traditional startups? The core leadership challenges are remarkably similar across all sectors, but the pace and complexity amplify everything. In emerging tech, you're dealing with technology that's evolving faster than most organizations can adapt, regulatory uncertainty that changes month to month, and technical sophistication that creates massive communication gaps between your engineering team and everyone else. What makes these sectors brutal is the compressed timeline. In traditional startups, you might have 18 months to figure out product-market fit. In crypto, market windows can close in 6 months. In AI right now, entire categories are being disrupted quarterly. This velocity doesn't give founders the luxury of gradually learning leadership skills. You're forced to evolve from technical founder to strategic leader while the ground is shifting beneath you, which is why so many brilliant builders become organizational bottlenecks. They're trying to maintain the deep technical involvement that made them successful while the company desperately needs them to focus on strategy, talent, and stakeholder management. The other challenge specific to emerging tech is that you're often explaining concepts to investors, customers, and team members who don't have the baseline knowledge to understand what you're building. In fintech, you're navigating complex regulatory frameworks while trying to move fast. In blockchain, you're fighting the assumption that everything crypto-related is a scam. These sectors demand founders who can translate technical innovation into business value for audiences who don't speak your language, which is a fundamentally different skill than building the technology itself. Looking back at all the founders you've worked with, what separates the ones who successfully scaled from the ones who became their company's biggest constraint? Honest self-awareness and the willingness to act on it. That's really what it comes down to. The scalers? They spot their blind spots early. Unfortunately, the CEOs who need this wake-up call most never get it. They'll always blame everyone else, turning their own ego and stubbornness into the anchor that sinks the ship.

Silicon Valley has lengthy worshiped its founders, the visionary engineers who flip caffeine and code into billion-dollar concepts. But what occurs when the similar brilliance that builds an organization begins to break it? Somewhere between the storage and the boardroom, many founders uncover that management isn’t just one other downside to remedy however an id disaster.

Audrey Nesbitt has seen that reckoning up shut. After years inside fintech, blockchain, and AI startups, she has watched gifted builders lose their corporations not to competitors however to themselves. Her new e book, “Why You Shouldn’t Be the CEO (And Other Ways to Save Your Startup),” argues that innovation can’t compensate for a founder’s blind spots, and that the braveness to step again could also be the most underrated ability in tech.

In this dialog, Nesbitt dismantles one among Silicon Valley’s oldest myths: that the one that begins the firm ought to all the time run it. She explains why actual management usually begins the second you notice it won’t be you.

Your e book questions one among the startup world’s oldest assumptions: that the one that begins an organization must also run it.  What made you need to problem that uncomfortable reality?

I stored seeing sensible founders provide you with highly effective concepts and get early traction, solely to lose momentum when it was time to scale. Not as a result of the imaginative and prescient wasn’t robust, however as a result of they struggled with management. The abilities wanted to encourage a staff, handle buyers, and navigate progress are fully completely different from the abilities that get a product off the floor.

After years of working with startups in fintech, blockchain, and AI, I noticed the similar story play out. Founders who beloved fixing advanced issues however dreaded managing individuals. Builders who have been sensible with code however prevented gross sales conferences and technique classes. Many took on the CEO title as a result of it felt anticipated or as a result of they felt entitled to it. In some methods, they have been. They began the firm, in any case. But that doesn’t all the time make them the greatest particular person for the function. Sometimes it’s ego that retains them there, not alignment.

I’ve additionally labored with founders who by no means wished the CEO function. They knew the place their strengths really have been and had little interest in pretending in any other case. One stayed centered on product and innovation whereas another person led the firm, and it scaled sooner due to that readability. Another advised me later, “I wasn’t CEO.” He’s now a profitable investor who discovered the place he creates the most worth.

The CEO function isn’t about being the smartest or most technical particular person in the room. It’s about main individuals, constructing partnerships, and making laborious enterprise selections. Those are completely completely different muscular tissues from constructing merchandise.

I wrote this e book to problem founders to ask themselves an uncomfortable query: Do you need to be CEO since you are the greatest particular person for it, or as a result of your ego says you need to be?

And it’s not a query you ask as soon as. You ought to ask it at each stage of progress. You may be the proper CEO in the starting and never at scale, otherwise you may develop into the function later. The secret is staying sincere about the place you add the most worth.

The greatest founders know management isn’t about holding a title. It’s about doing what’s proper for the firm and the imaginative and prescient you set out to construct.

You level out that almost two-thirds of high-potential startups fail due to founder battle, not poor merchandise. Why is it so laborious for founders to see after they’ve turn out to be a part of the downside?

That 65 p.c determine comes from Harvard’s Noam Wasserman, who argues in The Founder’s Dilemma that battle amongst founders is the root reason behind failure for a lot of promising startups.

Founders wrestle to see themselves as the downside as a result of they’re deeply invested of their id as the builder or visionary. Admitting it’s possible you’ll be the constraint looks like admitting defeat.

They develop blind spots that defend their ego; rationalizing management as “high quality,” framing micromanagement as “requirements,” or blaming exterior elements as a substitute of proudly owning inner dysfunction.

Conflict usually hides underneath the guise of imaginative and prescient alignment or tradition upkeep. It doesn’t really feel like a struggle; it looks like doing what wants doing.

And way over being a failure of character, it’s a failure of construction and suggestions. Founders typically lack goal frameworks to consider their influence, and asking for assist looks like a weak spot.

To be self-aware, founders want a shift in id: care extra about the firm’s consequence than their very own picture. Hire individuals who’ll inform you the reality. Build suggestions loops. And at each inflection level, ask: am I enabling progress or turning into a bottleneck?

The proper chief at the begin isn’t all the time the one to take the firm to scale, you write. How does a founder know when it’s time to hand over the reins or at the very least loosen their grip?

Founders usually romanticize the thought of being the everlasting captain of the ship, however scaling an organization is a brutal Darwinian course of the place ego is the first casualty. The reality is, most founders aren’t wired for each part of progress. Your scrappy, visionary hustle that bootstraps a startup from a storage to $10M in income can turn out to be a legal responsibility whenever you’re pushing towards $100M or an IPO. The “proper chief at the begin” is normally a chaotic inventor; the scaler wants a disciplined operator who obsesses over processes, expertise pipelines, and threat mitigation. Recognizing {that a} mismatch isn’t a failure; it’s self-awareness with emotional maturity. But brutal honesty: denial is epidemic, and loads of founders cling on till the board (or buyers) phases a velvet-gloved coup, like Travis Kalanick at Uber or Adam Neumann at WeWork. They don’t “hand over the reins”; they’re pried unfastened, usually with a fats payout.

The smartest founders don’t wait to be pushed. They herald operators, rent a president or COO, and check what it looks like to let go of management earlier than somebody forces the concern. They deal with succession as a method, not a punishment.

Many technical founders take satisfaction of their perfectionism and management. How do those self same traits that helped them construct their product find yourself holding the firm again?

Technical founders usually fall in love with their perfectionism and that tight grip on each element. It’s what will get them by way of these brutal early days of constructing one thing from nothing. Back then, it was a superpower. You tweak each line of code, each button, each function till it not solely works however feels proper. That obsession pulls in your first customers and offers the firm its spark.

But when the firm begins to develop, that very same intuition quietly turns towards you. The habits that after saved the startup start to sluggish it down. Take product launches, for instance. You maintain again for yet another repair, yet another polish, whereas a competitor ships one thing tough and will get actual suggestions. By the time you launch your “good” model, they’ve already captured the viewers and set the commonplace. Watching that occur hurts, particularly when you already know your product may need been higher if it had simply reached the market sooner.

It exhibits up inside the firm too. You begin rewriting your staff’s work, second-guessing selections, and micromanaging as a result of issues aren’t precisely the way you’d do them. The staff loses momentum, good individuals depart, and selections that after took hours now take weeks. The firm that began as a nimble experiment turns into a slow-moving machine.

It’s a merciless twist. The traits that constructed the basis find yourself setting the limits. To scale, you will have to let go slightly, commerce precision for perspective, and belief others to carry the imaginative and prescient ahead. The founders who determine that out early are the ones whose corporations truly make it previous the rising pains.

In the e book, you define instruments like the Five-Point CEO Self-Assessment and The Three Phases of Founder Evolution. How can founders use these frameworks to keep self-aware as their corporations develop?

The Five-Point Self-Assessment forces founders to get brutally sincere about 5 crucial areas: the Energy Test (what drains you versus what energizes you), the Competence Test (the place are you really world-class), the Enjoyment Test (what does your ideally suited workday truly appear to be), the Five-Year Test (what would you like to be identified for), and the Influence Test (do individuals observe you due to your imaginative and prescient or simply since you’re the boss). Most founders by no means ask themselves these questions till it’s too late. They’re so busy executing that they don’t discover they’ve been depressing in the CEO function for 2 years. The framework works as a result of it’s not about whether or not you are able to do the job, it’s about whether or not you must. There’s an enormous distinction between functionality and optimum match.

The actual energy of those frameworks is that they provide founders permission to be sincere with themselves with out it feeling like failure. You can take a look at the evaluation outcomes and acknowledge that you just’re spending 60% of your time on actions that drain you, notice you’re in the unsuitable part on your firm’s dimension, and make strategic selections about your function primarily based on information fairly than ego. The purpose isn’t to power your self into the CEO function if it’s not the proper match. The purpose is to optimize for the place you add the most worth, whether or not that’s as CEO, CTO, President or Chief Product Officer. Sometimes the greatest management determination is recognizing when another person must be main.

You’ve led groups throughout fast-paced, high-pressure industries, together with fintech, blockchain and AI. Do these sectors create completely different management challenges than conventional startups?

The core management challenges are remarkably related throughout all sectors, however the tempo and complexity amplify all the pieces. In rising tech, you’re coping with expertise that’s evolving sooner than most organizations can adapt, regulatory uncertainty that adjustments month to month, and technical sophistication that creates huge communication gaps between your engineering staff and everybody else.

What makes these sectors brutal is the compressed timeline. In conventional startups, you may need 18 months to work out product-market match. In crypto, market home windows can shut in 6 months. In AI proper now, whole classes are being disrupted quarterly. This velocity doesn’t give founders the luxurious of progressively studying management abilities. You’re compelled to evolve from technical founder to strategic chief whereas the floor is shifting beneath you, which is why so many sensible builders turn out to be organizational bottlenecks. They’re attempting to keep the deep technical involvement that made them profitable whereas the firm desperately wants them to give attention to technique, expertise, and stakeholder administration.

The different problem particular to rising tech is that you just’re usually explaining ideas to buyers, clients, and staff members who don’t have the baseline data to perceive what you’re constructing. In fintech, you’re navigating advanced regulatory frameworks whereas attempting to transfer quick. In blockchain, you’re preventing the assumption that all the pieces crypto-related is a rip-off. These sectors demand founders who can translate technical innovation into enterprise worth for audiences who don’t converse your language, which is a basically completely different ability than constructing the expertise itself.

Looking again in any respect the founders you’ve labored with, what separates the ones who efficiently scaled from the ones who grew to become their firm’s greatest constraint?

Honest self-awareness and the willingness to act on it. That’s actually what it comes down to. The scalers? They spot their blind spots early. Unfortunately, the CEOs who want this wake-up name most by no means get it. They’ll all the time blame everybody else, turning their very own ego and stubbornness into the anchor that sinks the ship.

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