Psychological Underpinnings of Founder’s Dilemma

In the previous article, we looked at the various strategies that can be used to overcome the Founder’s Dilemma to establish startup success. In this part, we look at the psychological underpinnings of the founder’s dilemma and how to overcome them. To effectively address the Founder’s Dilemma, it is crucial to understand the psychological factors […]

January 7, 2024

In the previous article, we looked at the various strategies that can be used to overcome the Founder’s Dilemma to establish startup success. In this part, we look at the psychological underpinnings of the founder’s dilemma and how to overcome them.

To effectively address the Founder’s Dilemma, it is crucial to understand the psychological factors that underlie strategic decision making in the entrepreneurial context. The very nature of founding a startup often means dealing with ambiguity, uncertainty, and high-stakes decisions. The following psychological aspects shed light on why founders may find themselves in dilemmas.

1. Navigating the Entrepreneurial Tightrope: Risk Aversion vs. Risk Taking

In the intricate landscape of entrepreneurship, founders find themselves walking a tightrope stretched between the opposing forces of risk aversion and risk-taking—a tension that embodies the very essence of the founder’s dilemma.. Getting a good grip on this balancing act leads to effective decision making in startups who are willing to go this journey.

The Yin and Yang of Risk:

The founder’s dilemma surrounding risk is not a binary choice but a delicate interplay between risk aversion and risk-taking. Risk aversion, a natural instinct ingrained in the DNA of entrepreneurs, serves as a protective shield for the venture. Heightened risk aversion can also be a symptom of having made mistakes in business ventures previously. 

However, like the yin seeking balance with the yang, excessive risk aversion can become a double-edged sword. The protective shield morphs into a stifling barrier, shielding the venture not just from potential risks but also from the very opportunities that drive innovation and growth. This overcautious stance can lead to missed chances, stagnation, and a failure to adapt to the ever-evolving business landscape, which is among a myriad common small business mistakes.

The Perils of Unchecked Risk-Taking:

On the flip side of the coin lies unchecked risk-taking—a bold, adventurous spirit that propels founders into uncharted territories. While this risk-taking mentality is essential for innovation and breakthroughs, the founder’s dilemma surfaces when it transforms into recklessness. Unchecked risk-taking can result in strategic decisions that, while daring, jeopardise the very viability of the company. It is a high-stakes gamble where the allure of potential rewards must be carefully weighed against the potential costs.

Striking the Right Balance:

The essence of the founder’s dilemma in risk management lies in striking the delicate balance between aversion and taking risks. Successful founders recognise that risk, when approached with strategic intent, is not a foe but a companion on the journey to success. The delicate dance involves:

  1. Calculated Risks: Distinguishing between reckless gambles and calculated risks is crucial. Founders must assess potential risks with a clear understanding of the associated benefits, ensuring that each risk taken is aligned with the overarching goals of the venture. Considering business lessons from previous experience – your own or others’ – is an important part of calculating risks.
  2. Risk Mitigation Strategies: Developing robust risk mitigation strategies is essential. This involves foreseeing potential challenges, creating contingency plans, and implementing safeguards that protect the company’s core assets while allowing room for experimentation and innovation, while avoiding the most common small business mistakes.
  3. Adaptive Decision-Making: Embracing an adaptive strategic decision making approach is key. The startup landscape is dynamic, and decisions made today may need adjustment tomorrow. Flexibility and responsiveness to changing circumstances allow founders to navigate uncertainties without succumbing to excessive risk aversion.

Cultivating a Risk-Aware Culture:

Beyond individual decisions, the founder’s dilemma in risk management extends to shaping the overall culture of the startup. Cultivating a risk-aware culture involves:

  1. Open Communication: Fostering open communication channels where team members feel empowered to voice concerns, share insights, and contribute to risk assessments. This also extends to getting good startup guidance from mentors and experts in the industry in which you operate.
  2. Learning from Failure: Embracing failure as a learning opportunity rather than a setback. A culture that views failures as stepping stones to success encourages calculated risk-taking.
  3. Celebrating Success and Learning: Recognising and celebrating successes resulting from well-calibrated risks while also learning from setbacks helps create a balanced perspective on risk. Your lessons learned are the most important takeaway from every experience your business and with it, you, go through.

2. Cognitive Biases: Navigating the Decision-Making Minefield in Entrepreneurship

In the labyrinth of entrepreneurship, where each of your strategic decisions can be a make-or-break moment, founders find themselves navigating a minefield fraught with cognitive biases. These mental shortcuts, such as confirmation bias and anchoring, are silent saboteurs that can cloud judgement and lead entrepreneurs down suboptimal decision paths. In this exploration, we delve into the intricate web of cognitive biases, emphasising the pivotal role they play in the startup strategic decision making journey and the imperative of mitigating their impact.

The Cognitive Minefield:

Imagine a founder enthusiastically pursuing a particular market strategy based on initial research. The confirmation bias might lead them to selectively gather or interpret data that supports this chosen path, ignoring warning signs or alternative perspectives. This tunnel vision can result in a skewed strategic decision making process, where only information confirming pre-existing beliefs is considered, potentially leading to flawed strategies and missed opportunities.

The Anchors of Decision-Making:

Anchoring is another cognitive bias that casts its shadow on strategic decision making. This bias involves relying too heavily on the first piece of information encountered when making decisions, even if it is irrelevant. For founders, anchoring can manifest when setting financial goals, determining the value of equity, or negotiating deals. If an initial valuation of the startup is set too low or too high, subsequent decisions tend to orbit around this anchor, potentially distorting financial strategies and negotiations.

Consider a founder who receives an initial, lower-than-expected valuation for their startup. Recognising and mitigating anchoring bias is essential for making strategic decisions based on current, relevant information rather than being tethered to irrelevant anchors.

The Impact on Adaptability:

The startup landscape is inherently volatile, requiring founders to be agile and adaptable in their decision-making. Cognitive biases, however, pose a significant challenge to this adaptability. This may be a case of learning the wrong business lessons at the initial stages of your startup venture, therefore impacting your startup negatively throughout its lifecycle.

For instance, a founder anchored to past successes might resist changing a product that has become outdated or unsuitable for the current market. Recognising and challenging these common startup mistakes and biases becomes paramount for fostering a culture of adaptability and innovation. 

Mitigating the Impact:

The first step in mitigating the impact of cognitive biases is awareness. Founders must recognise that these biases exist and can influence strategic decision making. This heightened self-awareness lays the foundation for implementing strategies to counteract the biases’ effects. The following are key approaches:

  1. Diverse Perspectives: Actively seek diverse perspectives within the team. Different viewpoints can utilise lessons learned by a range of individuals and can serve as a natural counterbalance to confirmation bias, helping founders consider a broader range of possibilities.
  2. Devil’s Advocate: Encourage the role of a devil’s advocate in strategic decision making discussions. Assigning someone to intentionally challenge prevailing opinions can uncover blind spots and mitigate the effects of confirmation bias.
  3. Data-Driven Decision-Making: Prioritise data over intuition. Implementing rigorous data collection and analysis processes helps mitigate biases by grounding decisions in objective information rather than subjective interpretations.
  4. Scenario Planning: Engage in scenario planning exercises that consider various outcomes and possibilities. This approach helps mitigate anchoring bias by encouraging founders to break free from fixed anchors and consider a spectrum of potential scenarios.
  5. Regular Reflection: Cultivate a habit of regular reflection on strategic decisions. Founders can assess whether biases played a role and, if so, identify strategies to counteract them in future decisions.

Real-World Implications:

Real-world examples abound with cautionary tales of founders falling prey to cognitive biases. Kodak, a once-dominant force in the photography industry, provides a striking illustration. Anchored to its success in film photography, Kodak dismissed the potential of digital photography despite emerging evidence. Confirmation bias led the company to focus on preserving its traditional business model rather than utilising lessons learned from the prevailing shift in technology, ultimately resulting in missed opportunities and a decline in market relevance.

In contrast, successful founders recognise the dangers of cognitive biases and actively work to mitigate their impact. Jeff Bezos, the founder of Amazon, is known for his emphasis on data-driven strategic decision making. By prioritising data over intuition and regularly challenging assumptions, Bezos has cultivated a culture that is less susceptible to the pitfalls of cognitive biases.

The Foundational Skill of Decision Making

Cognitive biases constitute a pervasive challenge in the founder’s strategic decision making journey, injecting a level of complexity that demands vigilant awareness and proactive mitigation strategies. 

Founders who master the art of startup strategic decision making in the face of cognitive biases not only navigate the minefield more successfully but also cultivate a foundation for sustained success. 

3. Founder’s Identity and Emotional Attachment: Navigating the Heart-Mind Dilemma

Founders often find themselves dancing on the fine line between their professional ventures and personal identities. This intimate connection is a double-edged sword—a source of unparalleled drive and commitment, but also a potential stumbling block when it comes to objective strategic decision making. 

The Deep Ties:

Founders, by the very nature of their entrepreneurial journey, forge deep emotional ties to their ventures. The startup is often not just a business entity; it becomes an extension of the founder’s identity—a manifestation of their dreams, values, and aspirations. This profound connection fuels the relentless drive to overcome challenges and transform visions into reality, ideally through business savvy gained by doing the proper research or utilising lessons learned from previous experiences. However, these deep ties can also create a blind spot, where emotional attachment clouds the lens through which entrepreneurial strategic decisions are made.

Fear of Failure:

One of the potent emotions that can influence startup strategic decision making is the fear of failure. Founders invest not just financial resources but also immense time, energy, and passion into their startups. The thought of failure becomes intertwined with their personal identity, creating a palpable fear that can drive decisions aimed more at avoiding failure than optimising success. 

Unwavering Commitment to a Vision:

While a steadfast commitment to a vision is often a strength, it can also transform into a vulnerability. Founders, driven by an unyielding belief in their vision, may resist altering course even when market dynamics suggest a need for adaptation. The emotional attachment to the original idea can blind them to opportunities for refinement and innovation, especially in terms of learning business lessons from similar entrepreneurs. 

The Emotional Decision Making Trap:

Emotions, while integral to the human experience, can become a decision making trap when they override rational assessments. Emotional strategic decisions are often reactive, driven by the immediate emotional impact of a situation, and may not align with the broader strategic goals of the startup. The founder’s dilemma lies in the balance between the passion that propels innovation and the emotional entanglements that can hinder objective decision-making.

Strategies for Navigating Emotional Attachment:

  1. Cultivate Self-Awareness: The first step in navigating the founder’s identity and emotional attachment is cultivating self-awareness. Founders must recognise and acknowledge their emotional ties to the startup, and actively reflect on how these emotions may be influencing their strategic decisions.
  2. Separate Personal Identity from Business Outcomes: While the success of the startup is deeply personal, it is crucial for founders to consciously separate their personal identity from the business outcomes. Acknowledging that failures or setbacks in the startup realm do not diminish personal worth can alleviate the fear of failure and is one of the most important business lessons that a startup founder can learn.
  3. Encourage Diverse Perspectives: As mentioned above, startup founders will do well to actively seek diverse perspectives within the team and external advisors. Different viewpoints can serve as a counterbalance to emotionally driven decisions, introducing a broader array of considerations.
  4. Establish Decision-Making Frameworks: Implement startup strategic decision making frameworks that incorporate both rational assessments and emotional intelligence. By establishing clear criteria for decision-making, founders can ensure that emotions are considered within a structured framework.
  5. Build a Support Network: Cultivate a strong support network of mentors, advisors, and peers. Having trusted individuals who can provide objective guidance can be invaluable in times when emotional attachment threatens to cloud judgement. Join a network such as the one we at Equity Match provide, where we give you access to a wide range of individuals who can teach important business lessons based on their successes and failures.

Real-World Consequences:

The consequences of emotional decision-making in the entrepreneurial realm are evident in numerous real-world examples. Blockbuster, once a giant in the video rental industry, clung to its traditional business model despite the rise of digital streaming. Unfortunately for Blockbusters, the lessons learned from its new technology heavy competitors were not heeded. The emotional attachment to the established way of doing business blinded Blockbuster to the transformative potential of emerging technologies, ultimately leading to its downfall.


  1. Wasserman, N. (2008). The founder’s dilemma. Harvard business review, 86(2), 102-109.
  2. Friedland, L. (2012). The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Start-Up.

Sutton, J. (2011). The consultant conundrum (the importance of hiring the right consultant to the success of a project). Strategic Direction, 27(2).