Asshole or Visionary? Navigating the Founder Mentality

AITA - Am I The Asshole?

Being a startup founder can feel like living on a roller coaster of passion, pressure, and pivoting. I've experienced exhilarating highs - turning a one-man web dev shop into a software consultancy grossing a third of a million per year in five years - and crushing lows, like watching a six-figure contract evaporate overnight. Throughout this journey, one question has haunted me: Does my relentless drive make me an asshole? On one hand, my blunt honesty and refusal to accept "good enough" push projects to success. On the other hand, that same intensity can alienate colleagues, friends, even romantic partners. This personal memoir examines the founder mentality - the unyielding passion and stubbornness that fuel entrepreneurs - and how it can both empower and hinder us. I'll share my story, draw on other founders' struggles (from Elon Musk to Mark Zuckerberg), and ask: is being an "asshole" part of being a visionary, and if so, how can we balance passion with empathy?

Early Sparks: Discovering My Drive

I never set out to run a business. In 2018, fresh out of high school, I had zero clue what to do with my life. Tech wasn't even on my radar - I assumed I wasn't "smart enough" for it. I enrolled in a Bachelor of Creative and Interactive Media almost by default, hoping to stumble upon something I loved. Surprisingly, I fell in love with everything: photography, graphic design, coding. I was a kid in a candy store of skills. Ultimately, I gravitated to web development, partly thanks to my mom. She'd once taught herself a bit of web work to update my parents' business site, and watching her opened my eyes to what was possible. That memory lit a spark in me.

First job, first lessons

I landed my first web developer job fresh out of uni. Despite being green, I was soon Head of Web at a small company public relations agency for a meager $50k salary. I threw myself into building their web division, even hiring a fellow uni student to join my team. I worked 7:00am to 3:00pm at the office (I wasn't big on hanging around chatting - just wanted to get things done), then another 5 hours every evening on side projects to sharpen my skills and start building my business. Within six months, my over-achieving paid off: I boldly asked for a raise to $80k and got it. I even negotiated a deal to sell the company web hosting and domains from my own fledgling business on the side. As my dad always taught me, "If you don't ask, you don't get." I had the audacity to ask, and it worked.

When that company got acquired, the new parent company unexpectedly made me Head of IT. Suddenly, at age 22, I was on $110k, reporting to executives and board members in a large investment firm. By all external measures, I was crushing it. But inside, I was miserable. I hated working for other people's agendas, especially when I spotted obvious stupidity in corporate decisions. I often found myself clashing with colleagues who had far more experience but, in my view, far less common sense or vision. The injustice of being blamed for problems outside my job scope, the bureaucracy, the slow pace - it drove me nuts. One colleague back then told me, not unkindly, "You have the same mentality as all the rich people. You'll do well... you're just an asshole." That comment stuck with me. It was both a compliment to my entrepreneurial drive and a critique of my abrasive style.

Looking back, I realise this period taught me a core trait of the founder mentality: an intense drive to do things better, which often comes with low tolerance for mediocrity. I had a burning desire to be my own boss, convinced I could run things without the "idiocy" I witnessed around me. That conviction might have made me seem arrogant (an "asshole", in plain terms), but it was born from passion and frustration, not malice.

Breaking Free: Betting on Myself

I eventually hit a breaking point. Despite the prestige and pay of my corporate role, I knew I couldn't keep working for others. I had proven to myself that I had the confidence and ability to build something on my own terms. So I quit. I took a "step back" in title, accepting a junior developer position at a small agency on Tamborine Mountain (at roughly the same pay, interestingly). It might have been a junior role, but it felt like freedom. Less responsibility for others' messes meant more energy to pour into my own venture. The agency's team was wonderful - supportive, creative, and the environment was a breath of fresh air compared to the corporate grind. I finally had breathing room to double down on my side business.

For a few months, life was balanced. I gave my 9–5 to the agency and my 5–midnight to my startup. I hustled hard, taking on any client I could find, often charging bargain-basement rates. I wasn't in it for profit at that stage; I was building a portfolio and a reputation. I even hired a fellow dev and a copywriter part-time to help with overflow work. It was exhausting, but exhilarating - I could see the foundation being laid for my own company.

Then, out of nowhere, I got laid off from the agency. Three months in, a crash in the crypto and gold markets hit some of their major clients, and I was the last in, first out. Suddenly the safety net was gone. But this twist of fate was exactly the push I needed. It was now or never: if I didn't go all-in on my business right then, I might never do it. As the shock wore off, I felt a steely resolve. This was my moment to bet completely on myself.

Highs, Lows, and Pivots

I officially went full-time with my own company in December 2022. It was terrifying and thrilling in equal measure. With laser focus, I started scaling up - turning my scrappy side-gig into a legitimate PTY Ltd company by the end of 2023 (a proud moment, incorporating my business). The hard work began to pay off. I moved from serving small local businesses (often friends who gave me a shot) to landing big clients with recognisable names. We're talking projects for multi-million-dollar organisations like Queensland Health and Mater Hospital. Suddenly, I had the clout and portfolio to pitch even larger deals.

The big contract: In 2023, I hit what I thought was the jackpot. I secured a six-figure annual contract to essentially build a tech startup in the gambling industry from scratch, alongside a partner. For all intents and purposes, I was a co-founder of that venture, employee #1, lead engineer. Over the next year I poured my heart and soul into it, treating that client's business like my own baby. With the influx of revenue, I hired multiple developers and a copywriter for my business to keep up with the existing workload; Tomedia grew fast. I won't delve into details (NDAs and the fact that the company got bought out and liquidated in a whirlwind of corporate drama), but let's just say it was an intense ride.

Then, just as quickly as it began, it was over. A cascade of unforeseen corporate battles at the client (the kind of high-stakes legal/financial maneuvering that makes for a Netflix drama) led to the project's termination. One day I was employee #1 of a rocket ship; the next day the rocket blew up on the launchpad. My six-figure revenue stream vanished overnight. In an instant, I had to lay off the team I'd built, sever contracts, and watch a year's work go up in smoke.

That failure stung. I'd put all my eggs (and a lot of capital) into that basket. Losing it shook my confidence and hurt financially. But here's where the founder mentality kicked in hard: I refused to see it as the end. Giving up was not an option. I licked my wounds and asked, What's the pivot?

I realised that what many clients valued most wasn't a full-service agency - it was me, my expertise and problem-solving, directly. So I reinvented my business as a consultancy focused on me as the brand. Instead of trying to scale up an agency with lots of overhead, I began contracting myself out as an interim CTO, a software engineer, a tech strategist - whatever high-value role a client needed to kickstart their project. For example, one of my favorite marketing agencies on the Gold Coast brought me in to teach their devs and build their new software capabilities, effectively leveraging my knowledge to uplevel their whole team. This approach clicked. It was more agile, more personal, and clients loved getting direct access to the "A-team" (me) rather than going through layers of account managers.

In the meantime, I also seized opportunities to co-found new ventures. I joined a friend from church as the CTO of a nascent startup (in a totally different industry), trading sweat equity for a stake in something I believe could be the next big thing. I started saying "yes" to more diverse streams of work - SaaS products I could build on the side, writing and thought leadership (hence this very memoir-style piece), even considering making educational courses since so many people ask me for advice. In short, I'm diversifying my bets and pushing my limits in every direction I can.

Financially, I set a crazy goal for myself: seven figures in revenue within two years. As of writing, I'm about one-third of the way there. It's an ambitious target, but that audacity and confidence fuel me. I don't care about money for money's sake - I've lived happily on very little before. What drives me is the challenge, the personal growth, and yes, maybe proving a point (more on that later). If I hit my goal, great. If not, I'll learn a ton along the way. Either way, I'm not going to fail because I won't stop until I succeed (or "pivot" the plan until it works).

Speaking of pivoting, one thing I've learned is that pivoting separates success stories from cautionary tales. To me, there's almost no such thing as a failed business - only founders who quit too early or are too stubborn to adapt. I was taught to never think I'm infallible. I've pivoted my business model multiple times, and each time it kept me alive. This isn't just my experience: nearly every great company has morphed from its original idea. Uber started as a black-car service and had to pivot into the low-cost UberX model to survive and scale (facing legal challenges along the way). Facebook's most famous pivot was in 2012–2014, when it shifted focus to mobile after its rocky IPO – a move so drastic and "gut-wrenching" but absolutely necessary, and it paid off massively. Google originally had no real business model beyond search; it pivoted by inventing AdWords and product listing ads, turning a great product into a money machine. Amazon went from selling only books online to becoming "the everything store" and even a cloud computing behemoth, AWS, which now powers much of the internet. The point is, adaptability is key. Pivoting saved those companies and it's saved mine. Stubbornness to pivot - clinging to a failing vision - is what truly kills businesses. Stubbornness to succeed, on the other hand, keeps you alive.

The Unyielding Drive (and Its Price)

If there's one trait all founders seem to share, it's an unyielding drive. I get super pumped about every project I dive into. I'm that guy who will research like crazy, devour new knowledge, and work round the clock to bring an idea to life. When I'm in that zone, it's like a trance: 12-hour workdays, 7-day weeks, completely immersing myself in the mission. This is not unique to me - founding a startup is often described as an extreme sport. You risk your life's balance and sanity for something most of the world finds "intangible, unquantifiable, downright stupid". And yet, you go for it because the drive inside you screams that it has to be done.

I tie my self-worth to my business's success in a way that outsiders might find unhealthy. Truth be told, if my company were to fail, it would feel like destroying a part of myself. Many founders have this "all or nothing" identity fusion; as one startup CEO put it, they make their business and self so interwoven that "to destroy their business is to destroy themselves". That kind of personal stake is a phenomenal motivator - failure simply isn't on the table. It's why you'll find me coding features at 2am or writing a proposal on a flight with no Wi-Fi, using every spare minute to push things forward. Elon Musk famously said, "Work like hell. You just have to put in 80 to 100 hour weeks. [This] improves the odds of success." If others work 40 hours, he noted, working 100 hours means you'll achieve in 4 months what takes them a year. I've taken that to heart. During the early growth of my business, my schedule was brutal: office job by day, startup by night, little sleep in between. Overwork? Possibly. Effective? Absolutely, at least in the short term.

However, this intense drive comes at a price. I've burned out more than once. I've had weeks where the stress and lack of sleep turned me into a zombie (or worse, an irritable jerk). Founders often "burn bright, flame out" because that "screw loose" of having something to prove drives them past normal human limits. In my case, I'm chasing not just money but a vision of who I can become. Maybe I do have "something to prove" - to those past bosses who didn't get it, to the peers who doubted me, or simply to myself. It's the classic founder mentality: whether the dream is "f-you money," changing the world, or just vindication, there's a fire under us that keeps us running at walls (or as one CEO described the startup life, willing to "eat glass and stare into the abyss" daily).

The people around me see the effects. Friends might wonder why I disappear for weeks. Family worries I'm overworked. And dating... well, let's just say being 100% consumed by a mission doesn't make for a balanced love life. Which brings me to how this mentality affects my personality - and why some people (including myself) wonder if I'm inadvertently being an asshole.

When Passion Turns to Obnoxious

Here's the uncomfortable truth: the same passion that makes me a great founder can make me difficult to be around. I'm obsessed with doing things the right way (or what I think is the right way). If someone - whether a client, an employee, or a friend - floats an idea that I find obviously flawed, I can't just smile and nod. I will bluntly tell them, "No, that's wrong, and here's why." I'll proceed to dismantle their proposal and then excitedly rebuild it in a better form, effectively saying, "Your original plan is dead, but look, we can pivot to this new approach instead!" I intend this to be helpful (I'm offering a path to success, not just criticism), but I'm aware that my delivery can come off as, well, obnoxious.

I've noticed that tact isn't my strong suit when I'm in "founder mode." I speak in absolutes: This will work. That will fail. Don't do that, do this. I've always believed that in business you must be malleable and brutally honest. I never assume I'm infallible - I'm constantly learning and open to being wrong - but I also don't sugarcoat what I do know. There's a mantra in startups: "strong opinions, loosely held." I've got the first part down (strong opinions for days!), but the "loosely held" part is a work in progress. If I know something from experience or extensive research, I will defend that point with ferocity. Sometimes I only realise later that I steamrolled someone's feelings in the process.

Case in point: I once hired a developer whose work consistently missed the mark. I couldn't understand why he couldn't just get it right the first time - especially when the requirements were clear. Over time, my frustration built up. I kept thinking, "If I can do this faster and better myself, why am I wasting time managing someone who can't deliver?" Eventually, I let him go. To him, I might've seemed impatient or overly critical. But in my mind, I was upholding the standard. Still, I sometimes wonder - was I too harsh? Maybe. But I've always believed excellence matters, and I struggle when others don't meet that bar.

Another example: explaining my work to my girlfriend (well, ex-girlfriend now, not surprisingly). She once offhandedly remarked that one of my business ideas sounded like "a waste of time." Ouch. My instinctive reaction was not to brush it off or calmly discuss it - I went into full lecture mode for three hours, passionately detailing every nuance she "hadn't thought of," every reason I knew the idea could work, why giving up is never on the table for me. It ceased being a conversation; it was a crusade. I imagine from her perspective I wasn't a boyfriend defending an idea - I was a zealot ranting and refusing to even consider that I might be wrong. That relationship didn't last, and I own my part in that.

The pattern is clear. My communication style under pressure can turn me into what looks like a classic jerk boss. I've tried to become more self-aware. I absolutely hate the idea of being a toxic "know-it-all." I want to help people, not tear them down. Yet time and again, I find my mouth racing ahead of my empathy when I'm convinced about a solution. I catch myself later and think, "I could have been gentler there. More diplomatic." It's a learning curve I'm still on.

Interestingly, I see much of myself in portrayals of famous tech founders. When I watched The Social Network, the dramatization of Facebook's origin, I related uncomfortably to Jesse Eisenberg's portrayal of Mark Zuckerberg: brilliant and driven, but socially oblivious and often dismissive of others. The show Super Pumped about Uber's founder Travis Kalanick similarly shows a leader whose passion curdles into arrogance. These depictions are exaggerated for Hollywood, but not entirely fiction. In real life, many visionary founders do exhibit abrasive behaviour. Are they assholes? Or just laser-focused on a vision most people can't see?

Visionaries or Jerks? Lessons from Famous Founders

If you feel like being called an "asshole" is part of founding a company, you're not alone. There's almost a trope that "all founders are a**holes." Let's look at a few famous examples to see why this perception exists:

Steve Jobs (Apple):

The late Steve Jobs is often held up as the archetype of the brilliant-but- abrasive founder. He was notorious for his temper and ruthless critiques. Early Apple employees recall how Jobs would openly insult work that didn't meet his standards. He was described as arrogant, demanding, and relentless. There's a story from the 1980s of Jobs telling an employee that their work was "shit" and summarily firing them on the spot. His "abrasive personality" and autocratic style created a toxic atmosphere that contributed to him being ousted from Apple in 1985. Yet, paradoxically, Jobs's uncompromising vision and high standards also pushed Apple to achieve things no one thought possible. After his exile, he matured, learned to communicate his vision better, and returned to lead Apple to its greatest innovations. By the time of the iPod/iPhone era, his passion was more tempered with purpose, though he was still no picnic to work for. Jobs himself acknowledged that being insanely demanding was part of how he drove excellence. As one Inc. profile put it, despite his abrasive style - or perhaps because of it - he built a world-changing company. This duality pretty much encapsulates the founder's dilemma: the very traits that make you great can also make you hard to deal with.

Mark Zuckerberg (Facebook):

In Facebook's early days, Zuckerberg could be shockingly brash. A famous anecdote from an early employee, Noah Kagan, illustrates this. Kagan and an engineer spent a month building a new feature to show Mark. During the demo, Mark abruptly pronounced "This is shit - redo it!" then dumped a bottle of water on the engineer's laptop and walked out. He also had a habit of wielding a samurai sword in the office, "fake- threatening" to chop off heads if someone pushed bad code that crashed the site. Bizarre as it sounds, this was a 22- or 23-year-old founder under extreme pressure, letting his frustration out in juvenile ways. Employees recall him saying things like "If you don't get that done sooner, I will punch you in the face" – meant in a joking way, but still... not exactly warm and fuzzy. Zuckerberg was (and maybe still is) an awkward introvert, laser-focused on growth. Professionalism and empathy were afterthoughts. Over time, Facebook brought in adult supervision (COO Sheryl Sandberg) to smooth out Zuckerberg's rough edges. But even in recent years, Facebook's culture has been criticised as toxic and predatory, reflecting some of Zuck's detached, "growth-at-all-costs" mentality. Zuckerberg is undoubtedly a visionary - he built one of the world's most influential platforms - but stories of him "shutting out his best friend" and generally exhibiting a "natural apathy toward people" have cemented an image of him as a bit of a jerk. He illustrates how a founder's intense focus on product and profits can lead to blind spots in understanding people. When employees say the pressure to pretend everything is great "is so great that it hurts", you know there's a leadership problem.

Travis Kalanick (Uber):

Uber's co-founder and former CEO, Travis Kalanick, might be the poster child for how toxic the founder mentality can become without checks and balances. Kalanick was aggressive, combative, and relentless. He drove Uber's explosive growth by bulldozing through barriers - legal, competitive, whatever. That "relentless competitiveness and aggressive personality" helped Uber reach a $68 billion valuation. In Uber's early culture, one of their core values literally was "Always Be Hustlin'," which translated into a cutthroat, win-at-all-costs environment. Kalanick himself set the tone: he famously chewed out an Uber driver who complained about falling fares, telling the driver "Some people don't like to take responsibility for their own shit" - all caught on a dashcam video. Internally, Uber under Kalanick was described as a "toe-stepping, cutthroat meritocracy" where solid results excused bad behavior. This led to scandals: allegations of widespread sexual harassment, intellectual property lawsuits, regulatory battles, you name it. Kalanick' s leadership style was both credited for Uber's success and blamed for its toxic culture. Eventually things went "a few steps too far" and even Kalanick had to admit it. Under investor pressure, he resigned in 2017. When he left, over a dozen top execs were also ousted, essentially acknowledging that the entire culture had rotted from the head. Uber brought in a new CEO to fix the culture, someone known as a good "people person" instead of a brilliant jerk. The Uber story teaches a crucial lesson: unchecked asshole behavior at the top will infect the whole company. Kalanick had many classic founder traits - strong-headed, passionate, "confidence bordering on arrogance" (as one article put it) - and those were arguably necessary to break into the heavily regulated taxi industry. But in today's world, that same bulldozing approach quickly turned into the perception (and reality) of being an arrogant, toxic leader. The balance was off.

Elon Musk (Tesla, SpaceX, etc.):

Elon is a more complicated case. He's undeniably visionary, having propelled multiple breakthrough companies. He's also built a reputation for being extremely demanding and often unreasonable in his expectations. Musk is known for setting insane deadlines and pushing employees to their limits. At Tesla, there were reports of 80-100 hour work weeks, with Musk himself often sleeping on the factory floor. He has fired people on the spot for giving what he deemed bad answers or for not achieving nearly impossible goals. Recently, after acquiring Twitter (now X), Musk gave employees an ultimatum via email: commit to an "extremely hardcore" workload, "long hours at high intensity," and "exceptional performance" or take three months' severance and leave. He said Twitter had to be rebuilt in a competitive world and that only people who would go "extremely hardcore" should stay. This kind of stance is thrilling to true believers and workaholics, but it's clearly not for everyone. It rubbed a lot of people the wrong way, and hundreds of employees quit rather than sign on to Musk's decree. In many ways, Musk embodies the extreme founder mentality: world-changing ambition, zero patience for dissent or mediocrity. He can be charming one moment and cutting the next. Some former employees laud his genius and work ethic; others describe him as mercurial or tyrannical. There's even been debate among leadership experts about whether Musk's abrasive, fear-based management style will backfire in the long run. Musk himself might not care - he's focused on results and assumes those who share his passion will put up with the "hardcore" culture. Time will tell if this makes him an asshole or simply a visionary who expects the extraordinary.

These examples show a pattern. As one article succinctly noted, "They were brilliant, and they were jerks." Jobs, Zuckerberg, Kalanick – all brilliant jerks in their own way. They had genius visions and got spectacular results, but they often "couldn't grasp what drove people". In other words, emotional intelligence lagged behind intellectual and strategic intelligence. Employees often hated working with them despite admiring their talents.

Why does this happen so frequently with founders? A big part of it is the intense pressure and personal investment we discussed earlier. When you're "staring into the abyss" of startup failure every day, you become desperate to win. The constant risk of death, plus tying your identity to the startup, can indeed turn a kind person into an "asshole" under stress. Founders often feel they alone carry the weight of the company. This mindset can lead to what some call the "brilliant jerk" syndrome – a leader who is insufferable interpersonally but continues to climb because they deliver results.

However, as these case studies show, being an asshole isn't a sustainable or healthy long-term strategy. Jobs got fired when his jerk side outweighed his contributions. Zuckerberg had to change (at least externally) and bring in support to avoid derailing Facebook. Kalanick's lack of people skills led to his downfall despite Uber's success. The era of toxic, tyrannical leaders may be fading, as employees have more avenues to expose and resist bad culture. In fact, management thinkers now emphasise empathy and communication as crucial leadership traits. You can be a tough, demanding founder without being a toxic jerk – but it takes self-awareness and effort.

So where does that leave me, and others like me, who are self-aware enough to ask: Do I really have to be an asshole to succeed? Or put another way, Is my stubborn dedication a good thing or a ticking time bomb?

Balancing Passion and People: Good or Bad?

The honest answer is that the founder mentality is a double-edged sword. My stubbornness, intensity, and refusal to accept failure have been incredibly good for my business success. They've allowed me to bulldoze through barriers and keep going when more reasonable folks might quit. As one leadership article noted, entrepreneurship often requires a "strong-headed, passionate leader to bulldoze through whatever barriers" and a "relentless competitiveness and aggressive personality to lead the way". Many great leaders have that "confidence bordering on arrogance" – it gives them the audacity to attempt the impossible. I take pride in having that audacity. Without it, I'd probably still be a junior dev at someone else's company, not a founder charting my own destiny.

On the other hand, the way I wield those traits can be very bad for my relationships and even for business in the long run. In today's work culture, people are less willing to tolerate an "arrogant asshole" boss, no matter how visionary. Being overly blunt or harsh can hurt my credibility, demotivate team members, and burn bridges with clients or partners. As much as I hate to admit it, there have likely been projects or deals I didn't win because I came off too strong in a meeting. My passion could be misread as inflexibility or ego. And that is on me to fix.

I do not want to become a toxic leader. Reading about the "brilliant jerks" who eventually face backlash or failure is a cautionary tale. The takeaway from Uber and others was clear: if a leader drives people with fear, anger, or disrespect, the company will suffer. I want to drive people with inspiration, knowledge, and positive energy - without losing my edge. To do that, I have to cultivate something founders like me aren't always great at: humility and empathy.

Being passionate doesn't mean I'm always right. I need to remind myself (and all fellow founders should too) that listening is as important as talking. I'm training myself to pause before reacting, to consider the human on the other side of the conversation. I'll never be a sugarcoater - that's not my style - but I can aim for candor with kindness. It's the difference between saying "This idea is garbage, do this instead" and saying "I see some issues with that approach; let's brainstorm a different direction." The content can be the same (we need a new approach) but the tone makes all the difference.

I'm also learning to surround myself with people who keep me in check. In the Jonny Burch article "Why's My CEO Being an Asshole?", he mentions how in later stages, founders have "seasoned executives" or trusted aides who act as "shit umbrellas" and help channel the CEO's craziness into a palatable vision. That resonated with me. I've begun to appreciate the role of a good project manager or operations head who can act as a buffer between my rapid-fire ideas and the team's capacity. These colleagues can tell me, "Hey, you're doing that thing again," when I'm too intense, or translate my directives in a more motivating way to others. Bringing in a complementary partner (like Zuckerberg did with Sandberg, or many tech founders do by hiring a solid COO) is a smart way to balance the equation.

Lastly, I want to address a fear I have: becoming a "guru." I expressed earlier that I hate "gurus" - those self-proclaimed entrepreneurship experts who spout generic advice without having truly built something themselves. They often have slick marketing, sell courses, and posture as visionaries, but there's no substance ("all the gear and no idea," as I put it). The irony is not lost on me that I'm here writing a reflective piece and people have suggested I create courses. The world probably has enough startup gurus; I don't want to add to the noise. If I ever share knowledge (in writing, videos, whatever), I want it to be real, grounded in my actual wins and losses, not recycled platitudes. Part of the founder mentality is authenticity - we are who we are, love us or hate us. If I start faking a persona just to broaden my appeal, I'd be betraying the very drive that got me here.

So, is being a stubborn, passionate founder good or bad? The nuanced answer: It's both, and it depends on self-awareness. Passion is good - without it, you won't survive the startup gauntlet. A willingness to be called an asshole (and even occasionally act like one in the service of your vision) can be a useful trait; it shows you're not here to win popularity contests, you're here to win period. Many successful founders have tread that line, sometimes stepping over it. But unchecked arrogance, zero empathy, and inability to change will eventually bite you in the ass. The key is to harness the positive aspects of the founder mentality (vision, perseverance, boldness) while actively curbing the toxicity that can come with it (insensitivity, ego, stubborn refusal to listen).

I'm trying to take this to heart. As one leadership coach wrote, "direct, stern, or passionate assertiveness is a legitimate leadership quality... within reason", but it can slide into "asshole territory" if not tempered with humility. The best founders learn to dial it up or down as needed. There are moments to be uncompromising - like upholding your core values or quality standards - and there are moments to be

flexible and supportive - like mentoring an employee through a mistake rather than chewing their head off. I'm learning that leadership is as much about emotional intelligence as it is about vision. In fact, the truly legendary founders seem to grow into that realisation. Jobs did, Gates did, many others.

At the end of the day, I refuse to let my business fail. That resolve will not change; it's my superpower. But I don't have to be a supervillain in the process. It's entirely possible to win big and not lose yourself or those around you. If I ever cross the line, I hope the people in my life will call me out, and I hope I'll have the wisdom to course-correct (a pivot in personal growth, you could say).

The founder mentality – this mix of dedication, obsession, and yes, stubbornness – is what separates those who dream from those who do. It's gotten me this far and I'm proud of it. I wear my passion on my sleeve, and if that sometimes labels me an asshole, so be it. But I'm not content with that label as an excuse. I believe we can be dedicated without being destructive. As I continue to push toward my goals (seven figures, new ventures, eventually becoming the investor who backs other crazy founders), I'll strive to keep my humanity in tandem with my ambition. Because succeeding at business but failing at being a decent human being is not success at all.

In the end, I don't think being an asshole is a prerequisite for success. Being relentlessly true to your vision is. And if you can do that while respecting others, you've mastered the founder mentality in the best way possible. It's a high bar to set - but hey, setting impossibly high bars is just what founders do, isn't it?

Resources used in this article:

The Pivotal Tale From Facebook's History https://magazine.wharton.upenn.edu/digital/the-pivotal-tale-from-facebooks-history/

Why's my CEO being an asshole? https://jonnyburch.com/why-s-my-ceo-being-an-asshole/

Elon Musk quote: Work like hell. I mean you just have to put... https://www.azquotes.com/quote/705674

Steve Jobs Showed 5 Leadership Habits That Still Separate Good Leaders From Bad Bosses Today https://www.inc.com/marcel-schwantes/steve-jobs-showed-5-leadership-habits-that-still-separate-good-leaders-from-bad-bosses-today/91142383

From Brilliant Jerk to Passionate People Person – Chief Learning Officer https://www.chieflearningofficer.com/2019/02/28/brilliant-jerks/

In Facebook's Early Days, Mark Zuckerberg Could Be a Jerk Boss https://www.inc.com/business-insider/how-zuckerberg-was-actually-a-jerk.html

What Uber's CEO Can Teach Us About Leadership – Chief Learning Officer https://www.chieflearningofficer.com/2017/03/09/what-ubers-ceo-leadership/

Elon Musk gives Twitter staff deadline to commit to being 'hardcore' | Elon Musk | The Guardian https://www.theguardian.com/technology/2022/nov/16/elon-musk-gives-twitter-staff-deadline-to-commit-to-being-hardcore

Elon Musk's fear-based management style doesn't work - Raconteur https://www.raconteur.net/leadership/elon-musk-fear-based-management