Ex-Banker’s Fintech Regret: Return to High Finance?

Startup Dream Turns Sour for Ex-Banker

A former investment banker, identified as ‘Bad Penny,’ is grappling with regret after leaving a decade-long career for a fintech startup that proved to be a major let-down. She is now seeking advice on how to credibly re-enter the high-stakes world of banking.

Bad Penny initially sought an ‘energising, buccaneering and entrepreneurial’ experience. However, her fintech venture is far from a ‘unicorn,’ with questionable equity and a failed primary product launch. The company’s main offering has become mundane training programs, a far cry from her expectations.

She openly admits to missing the dynamic trading floor, financial security, and the prestige associated with investment banking. The inadequate office facilities and her current situation have left her feeling embarrassed by her career pivot.

Coben’s Counsel: Re-entry is Possible

Columnist Craig Coben offers reassurance, stating that her career is not irrevocably damaged and her decision is not irreversible. He draws parallels to past instances where bankers successfully returned to high finance after failed internet start-ups in the late 1990s and early 2000s.

Coben highlights that the financial world tends to have short memories and understands the inherent high risks and rewards of start-up ventures. Therefore, failure in such an endeavor is generally not viewed negatively by potential employers.

A Three-Step Strategy for a Banking Comeback

Coben outlines a clear, strategic three-step plan for ‘Bad Penny’ to navigate her return to the banking sector:

• Check the Bridges: She should contact her former boss if she left on good terms, honestly explaining that she misses the bank’s environment and wishes to return.
• Plan B with a Headhunter: If her previous employer isn’t an option, she should engage a trusted headhunter. This allows her to discreetly explore opportunities at other firms, maintaining her dignity and providing candid feedback.
• Structure Her Narrative: When interviewing, she must avoid expressing shame or desperation. It’s crucial not to criticize her current employer. Instead, she should articulate her initial motivations for the start-up, the valuable lessons learned, and how the experience reinforced that her strengths are best utilized in investment banking. Coben likens her return to Simba reclaiming his place in ‘The Lion King.’