Article
The Alchemy of a Founder: Their Unique Blend of Traits Makes Them Startup Leaders
November 18, 2024
If you’ve ever met a founder—or better yet, spent time trying to understand what drives them—you’ll notice something right away: they’re wired differently. Founders think, act, and lead in ways that set them apart from the rest of us. They’re creative, fiercely independent, adaptable, and never afraid to challenge the status quo. These aren’t just personality quirks; they’re the traits that make founders uniquely suited to lead startups through the chaos and uncertainty of building something new.
Over the years, I’ve worked with and studied 122 founders. Through personality assessments, interviews, and 360-degree reviews, I’ve uncovered patterns that explain what makes these individuals tick. What I’ve learned is that their success isn’t just about being good at one thing—it’s about how a constellation of traits comes together to create something extraordinary.
Let’s explore what makes founders so different, and why their unique blend of traits is perfectly suited to turning bold ideas into reality.
1. Creativity: The Spark That Lights the Fire Founders are, above all else, creators. Their creativity isn’t limited to brainstorming product ideas or designing clever logos—it runs much deeper. It’s about how they see the world and solve problems. Founders are experts at divergent thinking, which is the ability to generate multiple solutions to a problem. Unlike most people, who might look for the “right” answer, founders explore every possibility, often discovering connections that others miss.
One founder I worked with described his process as “building a puzzle with pieces no one else knows exist.” He didn’t just see gaps in the market—he saw opportunities to redefine the rules entirely. This is how founders come up with ideas that feel inevitable in hindsight but revolutionary in the moment. Think of how Airbnb reimagined travel or how a small fintech founder rethought home mortgages by asking, “Why does this process still feel like it’s stuck in the 1980s?”
This creativity doesn’t just happen in isolation. Founders draw inspiration from everywhere—other industries, conversations with customers, even random insights while taking a walk. They’re constantly feeding their minds, which is why their ideas often seem larger-than-life.
But creativity can also be a curse. Many founders struggle with what I call “idea overload.” They generate so many concepts that it’s hard for their teams to keep up. One founder I studied was described by his team as an “idea machine who never turns off.” While this made him a visionary, it also led to frustration when priorities shifted too frequently. The best founders learn to harness their creativity by building systems that help them filter and focus their ideas.
2. External Focus: Tuning into the World Around Them Founders are often hyper-aware of what’s happening outside their companies. They’re not just focused on their own products or teams—they’re scanning the horizon for trends, customer feedback, competitor moves, and industry shifts. This external focus is one of their most powerful tools, helping them spot opportunities and adapt before it’s too late. In my research, I found that many successful founders make a habit of gathering insights directly from the world around them. One founder regularly sat in cafes and struck up conversations with potential customers, asking about their frustrations and dreams. Another spent many hours reading obscure industry reports, looking for trends others hadn’t noticed yet. These habits helped them stay ahead of the curve, turning raw observations into actionable insights.
This outward-facing mindset also makes founders excellent at connecting the dots between seemingly unrelated things. One founder noticed that social media influencers were starting to dominate consumer attention and thought, “What if we built a product that turned influencers into brand ambassadors?” That insight led to a company now worth hundreds of millions of dollars.
But there’s a downside to being so externally focused. Founders can sometimes get distracted by shiny trends or conflicting advice. The key is knowing what to filter out and what to act on. The best founders use their external focus not as a distraction, but as a compass, helping them steer their companies in the right direction.
3. Adaptability: Rolling with the Punches Starting a company is messy. Plans fail, markets shift, competitors emerge, and funding dries up. What separates founders who thrive from those who flounder is their adaptability—their ability to pivot, experiment, and learn from failure.
One founder in my research showed this adaptability in action during the early days of the pandemic. His business, which relied on in-person events, saw revenue plummet overnight. Instead of panicking, he quickly pivoted to virtual events, redesigning his entire business model in a matter of weeks. That ability to embrace change saved the company and even opened up new opportunities he hadn’t considered before.
This kind of flexibility doesn’t come naturally to everyone, but it’s second nature to most founders. They’re comfortable with ambiguity and uncertainty, and they see every challenge as an opportunity to iterate and improve. In psychology, this mindset is often linked to a trait called “tolerance for ambiguity,” which describes how well someone can function in uncertain or unpredictable environments.
However, adaptability has its limits. Founders who change course too often risk creating confusion and instability. One founder I studied was so quick to pivot that his team joked they should call him “Captain Whiplash.” The lesson here? Adaptability is a superpower, but it needs to be paired with focus and consistency to be effective.
4. Challenging the Status Quo: Rebels with a Vision Founders don’t just accept the world as it is—they challenge it. They see rules, norms, and conventions as opportunities to innovate. This rebellious streak is often what pushes them to start companies in the first place.
One founder in my research built her business around a simple question: “Why hasn’t this been done differently?” She wasn’t content to accept the inefficiencies and frustrations of her industry. Instead, she set out to create something better, rallying her team and customers around a vision of what could be.
This ability to challenge the status quo isn’t just about being contrarian. It’s about seeing possibilities that others can’t—or won’t—imagine. Founders don’t break rules for the sake of it; they do it because they believe there’s a better way.
But being a rebel isn’t always easy. Founders who constantly push for change can sometimes overwhelm their teams or struggle to gain buy-in. The best leaders know how to channel their disruptive energy in ways that inspire, rather than alienate, those around them.
5. Independence and Nonconformity: Marching to Their Own Beat If there’s one thing most founders have in common, it’s their fierce independence. They’re not the type to wait for permission or follow someone else’s playbook. Instead, they carve their own paths, often defying expectations along the way.
This independence is closely tied to their nonconformity. Founders aren’t afraid to stand out, think differently, or challenge authority. They bristle at bureaucracy and reject anything that feels too rigid or confining. For them, starting a company isn’t just about building a business—it’s about creating a world where they can thrive on their own terms.
This independent streak can be a double-edged sword. On the one hand, it gives founders the courage to take risks and pursue bold ideas. On the other hand, it can make them difficult to work with. One founder I studied was so resistant to collaboration that his team described him as “a lone wolf who refuses to run with the pack.” Over time, he learned to balance his independence with a willingness to listen and delegate, transforming his leadership style in the process.
6. The Alchemy of Traits: Where the Magic Happens What makes founders truly extraordinary isn’t any one trait—it’s the combination. Their creativity drives their vision. Their external focus keeps them grounded in reality. Their adaptability helps them navigate challenges, and their willingness to challenge the status quo pushes them to innovate. Independence gives them the grit to pursue their ideas, even in the face of doubt.
But here’s the real magic: these traits don’t exist in isolation. They interact in complex ways, creating a leadership style perfectly suited for the chaos and uncertainty of startups. For example, a founder’s creativity might fuel their adaptability, helping them come up with new solutions when things go wrong. Their independence might complement their rebellious streak, giving them the confidence to challenge norms and take bold risks. The result is a leader who isn’t just capable of starting a company, but of leading it through the ups and downs of growth, competition, and change.
A Few Final Thoughts The founders I’ve studied are far from perfect. Their traits can sometimes cause friction, and their leadership styles aren’t always easy to work with. But it’s precisely their quirks, contradictions, and complexities that make them who they are. They’re dreamers, doers, and disruptors. And in a world that often rewards conformity, they remind us of the power of thinking differently.
So, if you’re an aspiring founder—or just someone looking to lead with more creativity and boldness—embrace your unique blend of traits. Lean into your creativity. Stay tuned to the world around you. Adapt when you need to. Challenge assumptions. And most importantly, don’t be afraid to march to your own beat. After all, the best ideas often come from the people who refuse to fit the mold.
Over the years, I’ve worked with and studied 122 founders. Through personality assessments, interviews, and 360-degree reviews, I’ve uncovered patterns that explain what makes these individuals tick. What I’ve learned is that their success isn’t just about being good at one thing—it’s about how a constellation of traits comes together to create something extraordinary.
Let’s explore what makes founders so different, and why their unique blend of traits is perfectly suited to turning bold ideas into reality.
1. Creativity: The Spark That Lights the Fire Founders are, above all else, creators. Their creativity isn’t limited to brainstorming product ideas or designing clever logos—it runs much deeper. It’s about how they see the world and solve problems. Founders are experts at divergent thinking, which is the ability to generate multiple solutions to a problem. Unlike most people, who might look for the “right” answer, founders explore every possibility, often discovering connections that others miss.
One founder I worked with described his process as “building a puzzle with pieces no one else knows exist.” He didn’t just see gaps in the market—he saw opportunities to redefine the rules entirely. This is how founders come up with ideas that feel inevitable in hindsight but revolutionary in the moment. Think of how Airbnb reimagined travel or how a small fintech founder rethought home mortgages by asking, “Why does this process still feel like it’s stuck in the 1980s?”
This creativity doesn’t just happen in isolation. Founders draw inspiration from everywhere—other industries, conversations with customers, even random insights while taking a walk. They’re constantly feeding their minds, which is why their ideas often seem larger-than-life.
But creativity can also be a curse. Many founders struggle with what I call “idea overload.” They generate so many concepts that it’s hard for their teams to keep up. One founder I studied was described by his team as an “idea machine who never turns off.” While this made him a visionary, it also led to frustration when priorities shifted too frequently. The best founders learn to harness their creativity by building systems that help them filter and focus their ideas.
2. External Focus: Tuning into the World Around Them Founders are often hyper-aware of what’s happening outside their companies. They’re not just focused on their own products or teams—they’re scanning the horizon for trends, customer feedback, competitor moves, and industry shifts. This external focus is one of their most powerful tools, helping them spot opportunities and adapt before it’s too late. In my research, I found that many successful founders make a habit of gathering insights directly from the world around them. One founder regularly sat in cafes and struck up conversations with potential customers, asking about their frustrations and dreams. Another spent many hours reading obscure industry reports, looking for trends others hadn’t noticed yet. These habits helped them stay ahead of the curve, turning raw observations into actionable insights.
This outward-facing mindset also makes founders excellent at connecting the dots between seemingly unrelated things. One founder noticed that social media influencers were starting to dominate consumer attention and thought, “What if we built a product that turned influencers into brand ambassadors?” That insight led to a company now worth hundreds of millions of dollars.
But there’s a downside to being so externally focused. Founders can sometimes get distracted by shiny trends or conflicting advice. The key is knowing what to filter out and what to act on. The best founders use their external focus not as a distraction, but as a compass, helping them steer their companies in the right direction.
3. Adaptability: Rolling with the Punches Starting a company is messy. Plans fail, markets shift, competitors emerge, and funding dries up. What separates founders who thrive from those who flounder is their adaptability—their ability to pivot, experiment, and learn from failure.
One founder in my research showed this adaptability in action during the early days of the pandemic. His business, which relied on in-person events, saw revenue plummet overnight. Instead of panicking, he quickly pivoted to virtual events, redesigning his entire business model in a matter of weeks. That ability to embrace change saved the company and even opened up new opportunities he hadn’t considered before.
This kind of flexibility doesn’t come naturally to everyone, but it’s second nature to most founders. They’re comfortable with ambiguity and uncertainty, and they see every challenge as an opportunity to iterate and improve. In psychology, this mindset is often linked to a trait called “tolerance for ambiguity,” which describes how well someone can function in uncertain or unpredictable environments.
However, adaptability has its limits. Founders who change course too often risk creating confusion and instability. One founder I studied was so quick to pivot that his team joked they should call him “Captain Whiplash.” The lesson here? Adaptability is a superpower, but it needs to be paired with focus and consistency to be effective.
4. Challenging the Status Quo: Rebels with a Vision Founders don’t just accept the world as it is—they challenge it. They see rules, norms, and conventions as opportunities to innovate. This rebellious streak is often what pushes them to start companies in the first place.
One founder in my research built her business around a simple question: “Why hasn’t this been done differently?” She wasn’t content to accept the inefficiencies and frustrations of her industry. Instead, she set out to create something better, rallying her team and customers around a vision of what could be.
This ability to challenge the status quo isn’t just about being contrarian. It’s about seeing possibilities that others can’t—or won’t—imagine. Founders don’t break rules for the sake of it; they do it because they believe there’s a better way.
But being a rebel isn’t always easy. Founders who constantly push for change can sometimes overwhelm their teams or struggle to gain buy-in. The best leaders know how to channel their disruptive energy in ways that inspire, rather than alienate, those around them.
5. Independence and Nonconformity: Marching to Their Own Beat If there’s one thing most founders have in common, it’s their fierce independence. They’re not the type to wait for permission or follow someone else’s playbook. Instead, they carve their own paths, often defying expectations along the way.
This independence is closely tied to their nonconformity. Founders aren’t afraid to stand out, think differently, or challenge authority. They bristle at bureaucracy and reject anything that feels too rigid or confining. For them, starting a company isn’t just about building a business—it’s about creating a world where they can thrive on their own terms.
This independent streak can be a double-edged sword. On the one hand, it gives founders the courage to take risks and pursue bold ideas. On the other hand, it can make them difficult to work with. One founder I studied was so resistant to collaboration that his team described him as “a lone wolf who refuses to run with the pack.” Over time, he learned to balance his independence with a willingness to listen and delegate, transforming his leadership style in the process.
6. The Alchemy of Traits: Where the Magic Happens What makes founders truly extraordinary isn’t any one trait—it’s the combination. Their creativity drives their vision. Their external focus keeps them grounded in reality. Their adaptability helps them navigate challenges, and their willingness to challenge the status quo pushes them to innovate. Independence gives them the grit to pursue their ideas, even in the face of doubt.
But here’s the real magic: these traits don’t exist in isolation. They interact in complex ways, creating a leadership style perfectly suited for the chaos and uncertainty of startups. For example, a founder’s creativity might fuel their adaptability, helping them come up with new solutions when things go wrong. Their independence might complement their rebellious streak, giving them the confidence to challenge norms and take bold risks. The result is a leader who isn’t just capable of starting a company, but of leading it through the ups and downs of growth, competition, and change.
A Few Final Thoughts The founders I’ve studied are far from perfect. Their traits can sometimes cause friction, and their leadership styles aren’t always easy to work with. But it’s precisely their quirks, contradictions, and complexities that make them who they are. They’re dreamers, doers, and disruptors. And in a world that often rewards conformity, they remind us of the power of thinking differently.
So, if you’re an aspiring founder—or just someone looking to lead with more creativity and boldness—embrace your unique blend of traits. Lean into your creativity. Stay tuned to the world around you. Adapt when you need to. Challenge assumptions. And most importantly, don’t be afraid to march to your own beat. After all, the best ideas often come from the people who refuse to fit the mold.
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Startup founders represent the ultimate paradox: celebrated for their innovative brilliance yet notoriously susceptible to failure. In reality, the difference between astronomical success and dismal failure boils down to a surprisingly consistent set of behaviors and personality traits. Drawing from extensive 360 feedback studies, personality assessments, and deep insights from Founders Keepers, we've unraveled exactly what separates winners from losers in the startup world. Myth-busting: Genius Jerks Rarely Prevail A common myth persists that successful founders must be narcissistic, domineering, and abrasive—the stereotypical "genius jerk." Yet, our rigorous analysis of data from 122 founders, comparing the top performers (at least 10X returns) with bottom performers (zero returns), decisively shatters this myth. Successful founders, contrary to popular belief, rarely succeed because of egocentric ruthlessness. Instead, they thrive due to their extraordinary adaptability, relationship-building skills, disciplined execution, and deep personal grounding. Meanwhile, unsuccessful founders often implode because of their rigidity, isolation, impulsivity, and inability to truly lead teams. Adaptability: The Endless Pursuit of Product-Market Fit Successful founders understand one critical truth: product-market fit isn't a finish line; it’s a continuous process. They show an exceptional ability to: Remain open to input, eagerly soliciting and integrating team feedback. Effectively manage resistance, empathetically addressing team concerns. Skillfully create buy-in, building commitment through transparency and genuine engagement. In contrast, unsuccessful founders typically fail due to rigidity. They stubbornly anchor themselves to outdated strategies, ignore valuable feedback, and react defensively to challenges, eventually becoming roadblocks in their own companies. Relationship Building: From Loners to Leaders A pivotal distinction lies in the ability to work effectively through others. Successful founders consistently excel in empowering their teams. They: Delegate effectively, granting autonomy while clearly defining expectations. Maintain trust through consistent behavior, integrity, and transparency. Develop robust emotional intelligence, adeptly managing conflict and strengthening team cohesion. Unsuccessful founders, on the other hand, struggle profoundly with delegation. Their chronic micromanagement erodes trust and morale, creating environments of fear and resentment. They often isolate themselves, failing to build genuine relationships, thus missing critical insights and innovations their teams could provide. Execution: Discipline Over Charisma Execution—arguably the most underrated pillar of startup leadership—truly separates winners from losers. Successful founders meticulously: Set clear, measurable, and achievable goals. Follow through relentlessly, holding themselves and others accountable. Create robust systems and processes to scale effectively. Conversely, unsuccessful founders typically suffer from chronic disorganization and impulsivity. Their inability to prioritize, constant pivots without strategic clarity, and poor follow-through generate chaos and stifle growth. Personal Grounding: Stability Amidst Chaos Perhaps most counterintuitively, successful founders exhibit deep personal grounding—a trait seldom highlighted in sensational startup narratives. They: Demonstrate emotional resilience, remaining composed under extreme stress. Exhibit patience, tolerating ambiguity and uncertainty with grace. Maintain optimistic yet realistic perspectives, avoiding destructive cycles of anxiety or panic. Unsuccessful founders, however, often spiral under pressure. Their volatility and emotional reactivity exacerbate crises, leading to poor decision-making and destructive interpersonal dynamics. Self-Awareness: The Hidden Driver of Success Underpinning all these traits is profound self-awareness—arguably the most critical competency of all. Successful founders consistently seek self-improvement, humbly recognizing their weaknesses and proactively addressing them. They actively solicit honest feedback, never fearing the vulnerability required for growth. Unsuccessful founders, conversely, often display a tragic lack of self-awareness. Their denial of shortcomings, defensiveness to feedback, and unwillingness to evolve ultimately doom their startups. Real-World Wisdom: Voices from the Trenches Beyond the data, the human stories captured in 360 feedback illustrate these differences vividly: Successful founders receive praise like, “He constantly solicits input, adapts swiftly, and builds deep trust. His humility makes everyone want to follow him.” Unsuccessful founders, by contrast, earn harsh critiques: “He ignores input, reacts defensively, and insists on controlling every detail. The team is disengaged and demoralized.” These narratives underscore the simple but powerful truth that the best founders aren't isolated geniuses—they’re skilled leaders who build environments where everyone can thrive. The Path Forward: Turning Insights into Action If you're a founder, investor, or leader within the startup ecosystem, confront these truths head-on. Assess yourself and your organization rigorously: Are you truly adaptable, or merely superficially agile? Are you empowering your team, or stifling their potential? Are you executing with discipline, or flailing with chaos? Are you grounded emotionally, or reactive and volatile? Are you genuinely self-aware, or defensively delusional? Final Thoughts Ultimately, founder success isn’t about flashy charisma or ruthless ambition. It’s about a disciplined commitment to growth—both personal and organizational. Embrace adaptability, deepen your self-awareness, and master the art of leadership grounded in trust and integrity. This is not merely good advice—it’s the proven difference between a startup’s spectacular success and its avoidable failure. What traits do you see defining successful and unsuccessful founders in your experience? Let's discuss!
We’ve all seen the headlines: visionary founders, celebrated one day, indicted for fraud the next. Elizabeth Holmes of Theranos, Sam Bankman-Fried of FTX, Trevor Milton of Nikola—each a cautionary tale. But why does this keep happening? More importantly, how can investors and venture capitalists spot the red flags before disaster strikes? After decades coaching startup founders and executives, and through intensive psychological profiling research in my book, Founders Keepers, it’s clear that the qualities which make founders extraordinary can also lead them into ethical peril. Ambition Gone Rogue Ambition is the engine of innovation, but when unchecked, it can spiral into something destructive. Elizabeth Holmes, once hailed as the next Steve Jobs, turned ambition into deception, sacrificing integrity for the illusion of success. Her willingness to misrepresent Theranos's technology eventually led to fraud convictions and a 11-year prison sentence. Similarly, Trevor Milton fabricated demonstrations of Nikola’s hydrogen-powered trucks, deceiving investors and regulators alike. Ambition that isn’t tempered by reality becomes toxic, pushing founders to prioritize appearances over substance. Narcissism and the Cult of Personality A striking number of fraudulent founders exhibit narcissistic traits. Narcissistic Personality Disorder (NPD) is disturbingly common among indicted entrepreneurs like Holmes, Adam Neumann, and Billy McFarland. These individuals have inflated self-worth, entitlement, and a troubling lack of empathy—traits that enable them to manipulate investors, employees, and markets. Adam Neumann’s charismatic leadership at WeWork masked a self-serving agenda. He leased his own properties to WeWork and indulged in extravagances funded by investor capital. His eventual downfall underscores a critical point: charisma and confidence, unchecked by accountability, can devastate companies. Pressure, Risk, and Rationalization Founders operate in pressure cookers. Investor demands, market competition, and internal expectations can distort ethical boundaries. Under such strain, founders rationalize questionable decisions—initially minor, then increasingly severe. Sam Bankman-Fried’s FTX saga exemplifies this slippery slope. Praised for his effective altruism, he secretly diverted customer funds into his own hedge fund, creating one of history’s largest financial implosions. Under extreme pressure to perform, ethical lines blurred into oblivion. The Dark Triad and Founder Psychology Research identifies a psychological pattern—the Dark Triad: narcissism, Machiavellianism, and psychopathy. Founders exhibiting these traits manipulate, charm, and dominate others effortlessly. Their moral compasses malfunction, viewing ethics as mere obstacles. Martin Shkreli of Turing Pharmaceuticals raised drug prices mercilessly, justified as smart business. He ultimately faced securities fraud charges. This combination of manipulative charm, moral disengagement, and ruthless pragmatism frequently ends in corporate ruin. Red Flags Investors Can’t Ignore VCs and investors must vigilantly recognize signals of potential ethical crises: Accountability Gaps: Founders who deflect blame, resist feedback, or evade responsibility when faced with failures. Deceptive Fluency: Founders who remain intentionally vague, changing narratives to fit different audiences, lack transparency, and dodge specifics. Weak Governance: Companies lacking robust financial controls, passive boards, or weak compliance protocols enable founder misconduct. Excessive Charm: Overly charismatic leaders who evade scrutiny, foster cult-like devotion, and dismiss ethical concerns as trivial. Case Study: When Good Intentions Go Bad Consider Charlie Javice the Frank founder. Desperate to sell her startup, she fabricated millions of fake users, deceiving JPMorgan into a $175 million acquisition. Ambition, pressure, and opportunity collided disastrously, underscoring that even well-intentioned founders can fall if ethical vigilance wanes. Prevention through Awareness and Systems To mitigate these risks, investors must foster cultures of accountability. This means: Rigorous Due Diligence: Deep vetting of founder histories, not just their pitch decks. Transparent Governance: Enforcing independent oversight, clear reporting, and stringent ethical guidelines. Balanced Teams: Encouraging founders to build leadership teams empowered to challenge decisions. Healthy skepticism, combined with robust systems, creates a strong firewall against unethical behavior. Redemption and Self-Awareness Not all troubled founders are irredeemable. Many need interventions—coaching, accountability partners, and structured feedback—to prevent ethical slippage. Self-awareness is key. Founders who reflect on their blind spots and acknowledge limitations have a far better prognosis. Investing Wisely Means Looking Deeper The stark truth for investors is this: brilliance without integrity is dangerous. Investing isn't merely betting on ideas; it's assessing character. The cost of ignoring red flags is staggering, not just financially, but reputationally and ethically. Ask yourself one simple question when evaluating founders: If they weren't successful, would their behaviors still seem acceptable? The answer reveals everything. The line between visionary and fraudster is thin. Vigilance, skepticism, and structured accountability are critical tools in protecting your investments—and ensuring the next headline isn't about your portfolio.
Founders live in a world of chaos. It’s exhilarating, intense, and downright terrifying. You’re constantly shifting between the thrill of new ideas and the crushing weight of responsibility. Every decision feels like a life-or-death moment for your company, and the stress is unrelenting. Yet, amid this madness, there’s one thing that determines whether you’ll thrive or crash and burn: personal grounding.
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