04/06
Fearless Drive

Obsessive ambition
Risk-seeker
Unstoppable momentum


Obsessive ambition
Risk-seeker
Unstoppable momentum

What is it?

When is it crucial in a company’s life journey?

Why founders fail

How to hone this skill

01
What is it?

The unstoppable force of ambition, with an obsessive commitment and minimal regard for personal security of all kinds. This is all about embracing risk and pushing forward relentlessly to achieve the vision, no matter the obstacles.

“I have a high tolerance for risk. To me, it is more similar to a video game. Once you reach a stage, then the next stage is naturally more difficult and brings complexity – you learn from it and you develop. So each challenge is like leveling up.”

Cesar Carvelho, CEO and Co-founder, Wellhub

Risk is something you actively seek, and you enjoy situations with an element of personal or professional risk. But the risks are not haphazard or reckless – they are made in pursuit of your vision.

“You can’t just take risks for the sake of it. That’s gambling. You need to calculate the reward and assess whether the risk is actually worth it.” Michelle Lu, CEO and Co-founder, Vsim.

However, it’s not always fearless. “The reality is a bit darker,” says Thomas Plantenga. Emotion drives action – and not always the pretty ones.

“Fearless is the wrong word. It’s almost like an agnostic drive. You can get drive out of fear, out of inspirational futures, out of pain [...] There is a real fear that you screw up, and that is a driver. It’s not a sexy thing. Fear, revenge, and wanting the other company to fail – those are not things that are inspirational to talk about. But it’s really real. [...] Sometimes, as a team, we come to the conclusion that we really want to beat another company. But it’s okay, because we’re humans. We have all these emotions. We have jealousy, we have competitive emotions. And they’re not pretty. Fear is not pretty. But it’s real and something you have to deal with.”

Thomas Plantenga, CEO, Vinted

And more than just deal with it. It’s a motivator. This fear drives you to deeply understand your business and market from bottom to top. Fear of failure, fear of being destroyed by your competitors drives thorough investigation of problems, details and, ultimately, how to win.

02
When is it crucial in a company’s life journey?

Risk at early-stage is easier because there is literally less risk. But as the organization grows, it's hard to make the tough decisions, whether it’s closing a failing market or to invest already strained resources into high-risk opportunities that might not pay out.

“I think resilience and success come from harnessing these darker forces in a positive way. When we turned around Vinted, for a year and half, practically every month, we could have gone under. If fear doesn’t fuel you, then you’re not resilient because it’s fucking scary. You might have to fire 200 people and close the company six months from now. That’s scary.” Thomas Plantenga, CEO, Vinted.

03
Why founders fail

They take risks only in areas where they are comfortable with it. Fearless Drive means taking bold risks even in areas outside of your comfort zone, whether that’s pushing back on investors or making unpopular but necessary decisions that upset your team. Seeking too much consensus, which slows decision-making and dilutes bold moves, can be a big issue here.

“I find a lot of founders in my circle who struggle with taking risk. It often comes down to not having a great sense of self-knowing and self-being. So start by taking away the emotion and fear away from it, and just look at it as a project. [...] Just keep challenging your thoughts to get to a place where fear is no longer part of the equation, and it’s just rational thinking.”

Salma Bakouk, CEO and Co-founder, Sifflet

04
How to hone this skill

  • Topline: Embrace bold risk-taking and personal uncertainty

    Greatness comes from embracing risks that challenge your comfort zones. It’s not enough to take risks in areas where you feel confident; fearless drive requires you to push beyond boundaries and embrace uncertainty. Being a fearless founder means acknowledging that bold decisions may lead to failure – but also to extraordinary breakthroughs.

  • Risk isn’t recklessness; it’s courage in motion. The discomfort of uncertainty is proof that you’re pursuing something bigger than yourself.

  • Reframe risk as the foundation of success

    Thought trap: “If I risk too much, I’ll lose what I’ve worked for.”
    Reframe: “Risking what I’ve built opens the door to building something even greater.”

    Thought trap: “If I fail, it will be the end of everything.”
    Reframe: “Failure is part of the journey to success – it’s the step before growth.”


  • Topline: Embrace bold risk-taking and personal uncertainty

    Greatness comes from embracing risks that challenge your comfort zones. It’s not enough to take risks in areas where you feel confident; fearless drive requires you to push beyond boundaries and embrace uncertainty. Being a fearless founder means acknowledging that bold decisions may lead to failure – but also to extraordinary breakthroughs.

  • Risk isn’t recklessness; it’s courage in motion. The discomfort of uncertainty is proof that you’re pursuing something bigger than yourself.

  • Reframe risk as the foundation of success

    Thought trap: “If I risk too much, I’ll lose what I’ve worked for.”
    Reframe: “Risking what I’ve built opens the door to building something even greater.”

    Thought trap: “If I fail, it will be the end of everything.”
    Reframe: “Failure is part of the journey to success – it’s the step before growth.”


Topline: Embrace bold risk-taking and personal uncertainty

Greatness comes from embracing risks that challenge your comfort zones. It’s not enough to take risks in areas where you feel confident; fearless drive requires you to push beyond boundaries and embrace uncertainty.

Being a fearless founder means acknowledging that bold decisions may lead to failure – but also to extraordinary breakthroughs.

Risk isn’t recklessness; it’s courage in motion. The discomfort of uncertainty is proof that you’re pursuing something bigger than yourself.

Reframe risk as the foundation of success

Thought trap: “If I risk too much, I’ll lose what I’ve worked for.”
Reframe: “Risking what I’ve built opens the door to building something even greater.”

Thought trap: “If I fail, it will be the end of everything.”
Reframe: “Failure is part of the journey to success – it’s the step before growth.”


Self-coaching techniques

  • Challenge the limits of your comfort zone

    Ask yourself: “Am I avoiding this risk because it’s unwise or because it feels uncomfortable?” and “What could I gain by stepping into the unknown?”

  • Visualize the bigger picture

    When fear arises, picture the outcome if you succeed. Remind yourself: “Taking this risk is how I create something extraordinary.” and “Even if I fail, I’ll grow and learn in ways that prepare me for the next challenge.”

  • Normalize uncertainty

    Treat fear as a companion, not a roadblock. When doubt creeps in, say: “This discomfort means I’m on the right path – it’s where growth happens.” and “Fear doesn’t define me; action does.”

  • Short-term focus

    This week, identify one bold decision or risk you’ve avoided due to fear. Take one small, intentional step toward it, even if it feels uncomfortable. For example, pursue an opportunity that feels “too big,” or make a tough call you’ve been delaying.

  • Long-term growth

    Over time, this approach trains you to see fear and discomfort as signals of meaningful progress. By embracing uncertainty and taking transformative risks, you’ll foster a mindset of boldness and adaptability, inspiring your team to follow your lead and scale beyond limitations.

  • Challenge the limits of your comfort zone

    Ask yourself: “Am I avoiding this risk because it’s unwise or because it feels uncomfortable?” and “What could I gain by stepping into the unknown?”

  • Visualize the bigger picture

    When fear arises, picture the outcome if you succeed. Remind yourself: “Taking this risk is how I create something extraordinary.” and “Even if I fail, I’ll grow and learn in ways that prepare me for the next challenge.”

  • Normalize uncertainty

    Treat fear as a companion, not a roadblock. When doubt creeps in, say: “This discomfort means I’m on the right path – it’s where growth happens.” and “Fear doesn’t define me; action does.”

  • Short-term focus

    This week, identify one bold decision or risk you’ve avoided due to fear. Take one small, intentional step toward it, even if it feels uncomfortable. For example, pursue an opportunity that feels “too big,” or make a tough call you’ve been delaying.

  • Long-term growth

    Over time, this approach trains you to see fear and discomfort as signals of meaningful progress. By embracing uncertainty and taking transformative risks, you’ll foster a mindset of boldness and adaptability, inspiring your team to follow your lead and scale beyond limitations.

Challenge the limits of your comfort zone

Ask yourself: “Am I avoiding this risk because it’s unwise or because it feels uncomfortable?” and “What could I gain by stepping into the unknown?”

Visualize the bigger picture

When fear arises, picture the outcome if you succeed. Remind yourself: “Taking this risk is how I create something extraordinary.” and “Even if I fail, I’ll grow and learn in ways that prepare me for the next challenge.”

Normalize uncertainty

Treat fear as a companion, not a roadblock. When doubt creeps in, say: “This discomfort means I’m on the right path – it’s where growth happens.” and “Fear doesn’t define me; action does.”

Short-term focus

This week, identify one bold decision or risk you’ve avoided due to fear. Take one small, intentional step toward it, even if it feels uncomfortable. For example, pursue an opportunity that feels “too big,” or make a tough call you’ve been delaying.

Long-term growth

Over time, this approach trains you to see fear and discomfort as signals of meaningful progress. By embracing uncertainty and taking transformative risks, you’ll foster a mindset of boldness and adaptability, inspiring your team to follow your lead and scale beyond limitations.

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Progressive Explorer