50 Shades of Fintech: Unveiling the Risks and Kinks of Entrepreneurial Styles

50 shades of fintech entrepreneur

Let’s face it, being a fintech entrepreneur can make you feel a bit bipolar.

In 2005, I received funding from 7 credit unions to start my first big company. We crushed it the first year, signing 20 credit unions and setting up a path where we doubled every year for 6 years. In our second round of financing, we raised a few million dollars to go capture market share.

However, 3 years later, though we weren’t profitable, our growth rate meant we needed more cash. The investors put the brakes on and pushed us to get profitable instead of gain market share and build our moat. This caused a huge change in style as we went from Regulatory Navigators and Risk Mavericks to Boot Strappers.

I’m not sure we ever really recovered. Even with that, we were fortunate to have multiple years of the same style. Sometimes the startup struggles to find a consistent long-term approach and style or maybe the market changes overnight.

The reality is the fintech landscape is an ever-changing terrain teeming with entrepreneurs who pivot, adapt, and evolve. While agility is often celebrated, frequent shifts in entrepreneurial styles can result in a myriad of symptoms that ripple through an organization. Recognizing these indicators can be the first step in assessing whether a change is strategic or chaotic.

This blog will delve into the symptoms that manifest when switching between entrepreneurial styles, define the ten prevalent styles, and finally discuss the ramifications of not adhering to a consistent entrepreneurial approach.

Symptoms of Switching Entrepreneurial Styles

When changing entrepreneurial styles, I’ve seen issues arise in 3 key categories: organization, operations, and stakeholders. Here are some of the main symptoms I’ve seen from each category:

Organizational Symptoms

  • Leadership Changes: Frequent rotations in the C-suite or key leadership roles often signal a change in entrepreneurial focus.
  • Policy Revisions: An overhaul of internal policies—from risk management protocols to HR guidelines—can indicate a strategic shift.
  • Strategic Re-alignment: Updates in business strategy, usually communicated through company meetings or memos, spotlight a change in focus.
  • Cultural Shifts: A shift from a risk-averse to a more aggressive risk-taking culture, for example, is a revealing symptom.

Operational Symptoms

  • Project Reallocation: The pausing, acceleration, or termination of existing projects often accompanies a change in entrepreneurial styles.
  • Budget Fluctuations: Significant changes in budget allocations, especially in key sectors like R&D or marketing, are telltale signs.
  • Resource Redistribution: A noticeable deployment shift in human and technological resources often follows a change in entrepreneurial styles.
  • Technology Overhaul: Changes in the technological infrastructure, such as new data analytics software, can be indicative.

Stakeholder Symptoms

  • Investor Communications: Increased frequency of investor updates, discussing strategy or risk profile changes, is a key symptom.
  • Customer Feedback: Alterations in customer engagement metrics or the type of feedback received are indicative.
  • Partnership Announcements: A surge or decline in collaborations or partnerships often signals a shift in entrepreneurial style.

Maybe some of those sound familiar. If so, here is a quick list of the ten most common styles of fintech entrepreneurs.

The Ten Types of Fintech Entrepreneurs

In my experience, you probably have a dominate style and a secondary style that is used to reconcile key decisions. Does one resonate?

  1. Bootstrappers: Prefer organic growth, starting with minimal capital and avoiding external financing.
  2. Risk Mavericks: Unafraid of high-stake gambles and venture into uncharted fintech terrains.
  3. Synergists: Seek partnerships with established financial institutions or other fintech firms to reduce risk.
  4. Serial Entrepreneurs: Multiple ventures under the belt, analytical, and data-driven.
  5. Scale Maniacs: Focused on rapid expansion, usually through venture capital.
  6. Niche Specialists: Target a specific fintech segment, aiming for a narrow but loyal customer base.
  7. Regulatory Navigators: Expertise in dealing with complex regulatory frameworks.
  8. Social Entrepreneurs: Driven by social objectives, focusing on sustainability and impact.
  9. Innovators: Invest heavily in R&D, pushing the boundaries of fintech possibilities.
  10. Opportunists: Agile and adaptive, quick to seize emerging trends or regulatory changes.

If it’s easy to see your primary and secondary style, the next thing to consider is what situations will cause you to change a style. How do you know when to stay true to your form and approach?

In my experience, alignment needs to start between the investors, the entrepreneur, and management. If these are not aligned through metrics, objectives, and plans, it causes a constant reevaluation of the meaning of life that makes it impossible for teams to be successful.

Risks and Impacts of Inconsistent Entrepreneurial Styles

When changing entrepreneurial styles, you may face challenges from the shift. And, as with any change, you may also face risks. These are a few of the biggest challenges and risks I’ve seen.


  • Strategic Inconsistency: Confuses both employees and stakeholders and hampers long-term planning.
  • Resource Misallocation: Renders existing resources ineffective or underutilized.
  • Operational Disruption: Requires significant internal restructuring, affecting regular operations.
  • Reputational Risks: Erodes stakeholder trust, affecting the venture’s credibility.
  • Regulatory Challenges: Opens the firm up to increased regulatory scrutiny.


  • Financial Risk: Strains company finances due to investment in new assets or technologies.
  • Market Risk: Risks alienating the existing customer base or losing market share.
  • Execution Risk: Increases the likelihood of project delays or failures.
  • Opportunity Cost: Forfeits potential gains that could have been achieved by sticking to a consistent style.

Conclusions and Takeaways About Entrepreneurial Styles

Switching between entrepreneurial styles can offer the adaptability required in the dynamic fintech sector. However, such transitions should be strategically calculated to avoid the labyrinth of challenges and risks that can ensue.

The key is to recognize the symptoms early, understand the nuances of each entrepreneurial style, and weigh the implications of not staying true to a chosen path. After all, in the fast-paced world of fintech, consistency isn’t about stagnation; it’s about strategic integrity and sustainable growth.

The hard thing as the leader is picking a path and knowing when to stick with it and when to change. Too little change is a problem, but too much can also work against you.

CU 2.0 leaders have founded, grown, and exited multiple fintechs and businesses.

If you want expert guidance on growing yours—or just want to talk shop with like-minded entrepreneurs—drop us a line here: https://cu2.wpenginepowered.com/fintech-service-inquiry/

Recent Posts