What different choices would fintech CEOs make in their leadership strategies if they could turn back time?

Writer’s note: This story is the second part of the series, ‘The Journey to Leadership’, spotlighting six fintech CEOs and their individual journeys. In the opening installment of the series, I highlighted the lessons these leaders have gathered and how their experiences have refined their perception of their roles and abilities. The second chapter of this series explores the ‘what ifs’ in the decisions these six fintech CEOs would have reconsidered if they could start over. Although a strategy that succeeded for one might not apply to another, sharing their reflections signifies how understanding and addressing individual strengths and weaknesses can lead to more successful outcomes.

Learning the ropes of the CEO role requires blending 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 navigate 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

Timing is critical when making decisions, according to Stephany Kirkpatrick, CEO and founder of Orum.

“The timing of when we founded Orum has a lot to do with my answer, because I think it would look different in another setting, but we’re essentially a pandemic baby — born in late 2019,” said Kirkpatrick.

Kirkpatrick shared how her experience building her company’s foundation 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 her company, while preparing to seek institutional capital during the Covid-19 pandemic, the path forward was filled with challenges and ambiguity. During this time, the team focused on refining its product and contemplated solving two significant issues simultaneously: the efficiency of money transfers and the development of innovative money movement solutions with effective risk management. 

Looking back, Kirkpatrick acknowledges that there needed to be a system designed to link their initial product to the subsequent APIs, which required them to adopt a new strategy for building that support. This helped her understand that concentrating on a single task is more effective than spreading her efforts too thin.

“The old adage is true, doing two things at once is infinitely harder than doing one and it’s best to get certainty on that primary initiative before you move on to the next thing. That was just a big learning,” Kirkpatrick added. “Even the most legendary CEOs and company builders will tell you this but sometimes you have to live and learn it yourself!”

Novo 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 first-of-a-kind challenge for CEOs at all levels, requiring rapid strategy shifts and novel solutions.

One significant challenge Rangel faced during this period was finding effective ways to communicate institutional knowledge across global teams, something that had previously occurred organically in a traditional five-day-a-week office setting.

Reflecting on what he would have done differently, Rangel said, “I would have had more systems and processes in place sooner for capturing and sharing institutional knowledge — with a focus on everything we’ve learned from day one about the problems our small business customers face, how Novo has historically approached solving these problems, and the successes and lessons we’ve learned along the way.”

The value of teamwork combined with transparency

CEO and co-founder of Mercury, Immad Akhund, believes that transparency with the team is essential. According to Akhund, a CEO should not withhold his/her challenges from the team simply because they are in a leadership position. Maintaining transparency in sharing struggles is as crucial as being transparent in other aspects of managing the firm, such as setting expectations and defining company goals. 

“When I was running my previous startup, I worried about distressing my team if things weren’t going exactly to plan,” said Akhund. “My assumptions got the best of me and I’d forget to account for the very resiliency of the people around me.” 

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

Emphasizing the importance of team dynamics, CEO and co-founder of Rho, Everett Cook noted, “A major focus for me is appreciating the human element of organization-building.”

Cook believes that team members should be valued for contributing a significant part of their lives to the mission because they believe in the founder(s) and the vision. However, it’s equally important to ensure that the right people are brought on board for the right reasons, as a cohesive team can weather the highs and lows of the company’s journey.

Getting the most value from your investments

Reflecting on earlier strategies, Colin Walsh, CEO and founder of neobank Varo Bank, believes that channeling more investment capital into monetization activities might have shortened Varo’s path to profitability. The pressing need to expand the user base at the time, however, constrained those 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 outcome of this approach would have made the company reach profitability faster.

Leadership grounded in conviction instead of success

For Max Levchin, Affirm’s CEO and co-founder, passion is the primary ingredient for the recipe for success. In fact, through his experiences, Levchin has come to value conviction over mere success – as he believes it is what sustains a founder or a leader through challenges. 

“I’m much more proud of my failed projects where I had 110% conviction than the mild successes where I had 90%,” he said.

He asserts that being passionate about your work makes it easier to persevere during difficult times and stay aligned with your vision. The journey to finding product-market fit can be like a 40-year trek through the desert, and without a belief in the importance of what one is creating, one might abandon the effort when things get rough. 

Levchin’s varied experiences, with its mix of successful and unsuccessful ventures, have taught him that finding one’s true calling is crucial and that the impact of success or failure depends on how deeply one cares about one’s mission.

“I’ve gone down a few rabbit holes I had no real passion for (social gaming! photo-sharing!) – I learned a lot about consumer psychology and met some amazing people, but when the products I built did not dent the universe, I wasn’t too upset – and that is a sign of a time wasted,” he noted. 

The insights of these fintech CEOs into their past strategies — what worked, what didn’t, and the lessons learned — highlight that each one 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 first installment in the series explored:

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