The Day After Success”: Business Leader Reveals Psychological Impact of Major Exit in Rare Candid Interview


Behind the champagne toasts and congratulatory messages that accompany major business exits lies a psychological reality rarely discussed in business media, i.e., the emptiness that follows success. In an unusually transparent interview on the Trending Diary podcast, former Tails Group owner Siddharth Shankar pulled back the curtain on the emotional aftermath of his $500 million exit.

“There was a feeling of happiness because I had messages, calls, emails pouring in… suddenly I had a lot more [supporters],” Shankar revealed. “Your cheeks are hurting because you've been smiling for too long, and then you keep your phone down and that content is not there.”

Shankar's revelation challenges the conventional narrative that business exits represent the ultimate entrepreneurial achievement. Instead, he describes a profound sense of disorientation after selling the business he had built over 15 years.

“For 15 years, I've got up in the morning and I've had something to do,” he explained. “And then one fine day, you get up in the morning and you're like, 'What do I do now?'”

Identity Beyond Business

The interview highlights a growing recognition among business psychologists that entrepreneurs often tie their identity closely to their ventures, creating significant adjustment challenges following exits. Shankar's experience aligns with research showing that founders frequently struggle with purpose and meaning after selling their companies.

“I sold the business because I wanted the best for the business, not for myself,” Shankar noted, suggesting that the decision came from recognizing his own limitations as the company's “bottleneck” rather than personal desire for an exit.

Family Influence on Business Philosophy

The podcast also explored how Shankar's government-service family background influenced his contrarian approach to business. Despite his family's initial opposition to his entrepreneurial path, their different perspectives shaped his leadership style.

“My mom was spontaneous, quick-witted, intuitive… My dad was more analytical,” Shankar recalled, describing how these complementary approaches informed his decision-making. This blend of intuition and analysis ultimately contributed to his unorthodox business model that eschewed external funding.

Leadership Transformation

Perhaps most striking was Shankar's reflection on his evolution as a leader. “I was not always like this,” he admitted when complimented on his calm demeanour. “If you met some of my friends and family, they'd tell you I was as hot-blooded as they come.”

This transformation from impulsive to measured leadership offers valuable insights for executives navigating high-pressure business environments and personal growth trajectories.

Shankar now serves as Global COO of Komerz while holding board positions with multiple private equity funds, demonstrating how business leaders can reinvent themselves following major exits.

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