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Difficult founder or reality distortion field ?

Derek Watson
Derek Watson

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What Is FinTech? The Basics

Difficult founder or reality distortion field?

🤔 Have you ever come across a founder who’s described as “Difficult”?
➡️ At first, this may seem like a 🚩, but there’s more to it than meets the eye. When it comes to reference checking for startup founders, “Difficult” is a word that deserves a deeper analysis.
💪🏼 The “Difficult” characteristic can mean polarizing, but if combined with self-awareness, it can be super power for a founder. It’s important to understand why they are “Difficult”, and if it stems from a desire to get shit done and bring their vision to life, versus being ultimately self-defeating.
➡️ The traits commonly associated with “Difficult” are often associated with brilliant as well:
🤝 Pairing a “Difficult” founder with a great co-founder who knows how to manage alongside them can result in a greater whole. Don’t forget to talk with this person to get their unique insights on the relationship.


  • Strong-willed and opinionated

    Individuals who have a determined and unwavering character, and who are not easily swayed by others' opinions or beliefs.

  • Drive for excellence and impact

    Individuals who are highly motivated to achieve great results and make a positive difference in their work or in the world around them. They are not satisfied with just meeting expectations, but rather strive to exceed them and create a meaningful impact.

  • Self-awareness

    Individual's ability to introspect and recognize their own thoughts, feelings, and behaviors. It involves being conscious of one's own strengths and weaknesses, as well as how their actions affect themselves and others.

  • Can be polarizing

    Individuals who are strong-willed and opinionated, and who have a drive for excellence and impact, may sometimes be divisive and create disagreement or conflict due to their strong convictions and beliefs. They may not always be universally liked or agreed with by others.

  • Visionary and innovative

    Individuals who are able to see and think beyond the current status quo, and who are constantly seeking new and innovative ways to solve problems or create value. They are able to envision a future that is different from the present and have the creativity and ingenuity to bring that vision to life.

  • Resilient and determined

    Individuals who have the ability to bounce back from setbacks and adversity, and who remain steadfast and persistent in the pursuit of their goals. They do not give up easily, and are able to stay focused and motivated even in the face of challenges and obstacles.

  • Strong communication skills

    Individuals who are able to effectively and clearly convey their thoughts, ideas, and messages to others. They are skilled at both verbal and nonverbal communication, and are able to adapt their communication style to effectively communicate with different people in various situations. They are also good listeners and are able to understand the perspectives of others.

  • Passionate and enthusiastic

    Individuals who have a strong and intense emotion or feeling towards something, and who are highly motivated and committed to their work or goals. They are able to inspire and energize others around them with their enthusiasm and optimism. They have a genuine love and excitement for what they do, which fuels their drive and determination.

  • Self-starter with a strong work ethic

    Individuals who are able to take initiative and work independently without constant supervision. They are highly motivated and have a strong sense of responsibility to deliver quality work on time. They are able to prioritize tasks and manage their time effectively, and have a high level of dedication and commitment to their work.

  • Ability to inspire and lead a team

    Individuals who are able to motivate and guide a group of people towards a shared goal or vision. They are able to communicate effectively, provide guidance and feedback, and foster a positive and collaborative team environment. They have the ability to identify and leverage the strengths of team members, and are able to create a sense of purpose and direction for the team.

💬 When you ask the “Difficult” founder about their reputation, it’s important to take a growth mindset, and see if they’re open to discussing it and improving. If they recoil or get defensive, it may be a red flag.
➡️ Ultimately, “Difficult” isn’t necessarily a deal breaker, but it requires a second set of questions to understand if the person can be a great leader/CEO and if you’re the best investor for them.

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