Author’s Note: This story is the second part of the series, “The Journey to Leadership,” which highlights six fintech CEOs and their individual journeys. In Opening of the installment of the series, I highlighted the lessons these leaders learned and how their experiences sharpened their sense of their roles and capabilities. The second installment of this series explores the “what ifs” in the decisions these six fintech CEOs would reconsider if they could do it all over again. While a strategy that worked for one might not work for another, sharing their insights suggests how understanding and addressing individual strengths and weaknesses can lead to more positive outcomes.

Learning the tricks of the CEO role requires mixing and balancing external guidance with personal experiences. Part of this journey also involves reflecting on leadership decisions, both past and present, to recognize areas for improvement. This reflection is not about dwelling on past actions, but about identifying better ways to address challenges with the knowledge gained over time and using that insight to guide future decisions.

One Thing at a Time and the Covid-19 Chapter

According to Stephany Kirkpatrick, CEO and founder of Gold.

“The timing of when we started Orum has a lot to do with my response, because I think it would have looked different in a different context, but we are essentially a baby born out of the pandemic, in late 2019,” Kirkpatrick said.

Kirkpatrick shared how her experience building the foundation of her company taught her the value of prioritizing one task before moving on to the next. She learned that when faced with uncertainty, it’s crucial to step back and pause until there’s a clear path forward.

In the early days of his company, as it prepared to seek institutional capital during the Covid-19 pandemic, the path forward was fraught with challenges and ambiguity. During this time, the team focused on perfecting its product and considered solving two significant problems simultaneously: money transfer efficiency and developing innovative solutions for money movement with effective risk management.

Looking back, Kirkpatrick recognizes that they needed a system designed to connect their initial product to subsequent APIs, which required them to adopt a new strategy for building that support. This helped her realize that focusing on a single task is more effective than spreading your efforts too thin.

“The old adage is true, doing two things at once is infinitely harder than doing one and it’s better to be sure of that primary initiative before moving on to the next thing. It’s just been a great learning curve,” Kirkpatrick added. “Even the most legendary CEOs and founders of companies will tell you that, but sometimes you have to live and learn it yourself!”

New CEO and founder Michael Rangel also encountered the challenges of running a startup during a time when the world had suddenly gone remote. This unprecedented shift to a fully remote work environment was a unique challenge for CEOs at all levels, requiring rapid strategy shifts and innovative solutions.

One of the biggest challenges Rangel faced during this time was finding effective ways to communicate institutional knowledge across global teams, something that had previously come naturally in a traditional five-day office environment.

Reflecting on what he would have done differently, Rangel said, “I would have implemented more systems and processes sooner to capture and share institutional knowledge, focusing on everything we’ve learned since day one about the problems our small business customers face, how Novo has historically approached solving those problems, and the successes and lessons we’ve learned along the way.”

The value of teamwork combined with transparency

CEO and co-founder of MercuryImmad Akhund believes that transparency with the team is essential. According to Akhund, a CEO should not hide his challenges from the team simply because he is in a leadership position. Maintaining transparency in sharing challenges is as crucial as being transparent in other aspects of running a business, such as setting expectations and defining company goals.

“When I ran my previous startup, I was worried that I would put my team in a difficult position if things didn’t go exactly as planned,” Akhund said. “My assumptions got the best of me, and I forgot to take into account the resilience of the people around me.”

In hindsight, Akhund wishes he had been more available to his team during difficult times. He has learned that treating information as a basis for broader discussions and framing setbacks as opportunities for collective effort is key to effective leadership.

Stressing the importance of team dynamics, CEO and co-founder of RhoEverett Cook observed, “For me, one of the main goals is to appreciate the human element in building an organization.”

Cook believes that team members should be recognized for contributing their lives meaningfully to the mission because they believe in the founder(s) and the vision. However, it is equally important to ensure that the right people are hired for the right reasons, as a cohesive team can weather the ups and downs of the company’s journey.

Get the most value from your investments

Reflecting on previous strategies, Colin Walsh, CEO and founder of the neobank Varo Bankbelieves that funneling more investment capital into monetization activities could have shortened Varo’s path to profitability. The urgent need to expand the user base at the time, however, limited such initiatives.

If Walsh could go back in time, he would “prioritize investments that have a more immediate and tangible impact on revenue and profitability, in order to improve operational efficiency and reduce costs.” He believes the result of this approach would have allowed the company to reach profitability more quickly.

Leadership based on belief rather than success

For Max Levchin, To assertCEO and co-founder of, passion is the main ingredient in the recipe for success. In fact, through his experiences, Levchin has come to value belief more than just success, as he believes it is what sustains a founder or leader through challenges.

“I am much more proud of my failed projects, in which I was 110 percent convinced, than of the moderate successes, in which I was 90 percent convinced,” he said.

He says that being passionate about your work makes it easier to persevere through difficult times and stay aligned with your vision. The journey to find product-market fit can be like a 40-year trek in the desert, and without belief in the importance of what you’re creating, you might abandon the effort when things go wrong.

Levchin’s diverse experiences, with their mix of successful and unsuccessful initiatives, have taught him that it is essential to find one’s true calling and that the impact of success or failure depends on how much one cares about one’s mission.

“I’ve delved into some areas that I didn’t really have a passion for (social gaming! Photo sharing!)—I’ve learned a lot about consumer psychology and met some amazing people, but when the products I’ve created don’t make a dent in the universe, I don’t get too upset—and that’s a sign of wasted time,” he noted.

The insights of these fintech CEOs into their past strategies, what worked, what didn’t work, and lessons learned, highlight that each of them has faced and continues to face unique challenges that cannot be addressed with a one-size-fits-all solution. Effective solutions come from recognizing and working on individual strengths and weaknesses.

The launch episode explored:

What lessons have fintech CEOs learned from mastering the art of leadership?

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