In a rare and introspective interview, Siddharth Shankar, the former owner and founder of Tails Group, revealed the profound psychological void he experienced after selling his company for $500 million. The revelation came during an episode of the Trending Diary podcast, where Mr. Shankar candidly discussed the emotional aftermath that followed what most would consider a dream achievement.
For over 15 years, Siddharth Shankar poured his energy, creativity, and determination into building Tails Group from the ground up. The company, known for its innovative approach to pet nutrition and digital customization, grew into a powerhouse under his leadership. The sale, which brought in a staggering half-billion-dollar valuation, appeared to mark a perfect entrepreneurial success story. But behind the scenes, Shankar faced a personal struggle that money could not resolve.
The Day After the Exit
Shankar painted a vivid picture of what life looked like after the sale. At first, the excitement overwhelmed him. Congratulatory messages, calls, and emails flooded his inbox. Friends and business associates praised his success, and for a brief moment, the high of recognition masked the deeper emotions stirring within.
“There was a feeling of happiness because I had messages, calls, emails pouring in… suddenly I had a lot more supporters,” he said on the podcast. “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.”
Once the initial excitement faded, the silence set in. The buzz of daily operations, the adrenaline of making crucial decisions, and the satisfaction of solving problems vanished overnight. Shankar described waking up the next morning and realizing, for the first time in 15 years, that he had no pressing responsibilities.
“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?’”
A Disorienting Emptiness
The emotional aftermath surprised even Shankar. Most people expect an exit like his to bring lasting euphoria and fulfillment. Instead, he encountered a strange and disorienting emptiness—one that success had never prepared him for.
He confessed, “There’s a strange emptiness that nobody warns you about.” The feeling went beyond boredom or temporary discontent. It stemmed from a lack of purpose—something that a daily mission and relentless entrepreneurial pursuit had always provided.
Many founders tie their identities closely to their ventures. Their routines, goals, and self-worth revolve around the business they build. When that anchor disappears, it often leaves a void too vast for wealth or accolades to fill. Siddharth Shankar’s experience illustrates this harsh truth with painful clarity.
The Reason Behind the Exit
Despite the emotional cost, Shankar insisted that he sold the business not for personal gain but for the company’s benefit. He believed he had become the “bottleneck” in its growth and wanted Tails Group to flourish beyond his capabilities.
“I sold the business because I wanted the best for the business, not for myself,” he clarified. This self-awareness pushed him to step aside, even though it meant letting go of something he had nurtured for over a decade.
Shankar’s decision reflected a deep understanding of leadership. He recognized that clinging to control would eventually harm the organization. By prioritizing the company’s long-term potential, he displayed a rare humility often missing in high-powered business circles.
Finding a New Purpose
After the sale, Shankar refused to remain idle. He began exploring new avenues to channel his energy and expertise. Today, he serves as the Global Chief Operating Officer at Komerz, a tech-driven commerce platform, and holds multiple board positions across various private equity firms.
This new chapter in his life does not mimic the intensity of building a startup from scratch, but it does offer fresh challenges and opportunities for growth. These roles have helped him rediscover a sense of direction, even if they don’t replicate the emotional highs of entrepreneurship.
Still, he admits that the transition remains ongoing. Finding purpose after an extraordinary exit takes time, especially when the previous mission defined one’s identity for so long.
The Human Behind the Success
Beyond business, the podcast gave listeners a glimpse into Shankar’s personal evolution. He shared stories about his family, revealing how their contrasting personalities shaped his leadership approach.
“My mom was spontaneous, quick-witted, intuitive… My dad was more analytical,” he said. These influences taught him to balance gut instinct with careful analysis—a combination that served him well in critical decisions.
He also reflected on his transformation as a leader. “I was not always like this. If you met some of my friends and family, they’d tell you I was as hot-blooded as they come,” he admitted with a laugh. Over time, maturity, experience, and setbacks molded his temperament and leadership style.
His candidness revealed a man unafraid to expose vulnerabilities. He didn’t present a glossy version of success. Instead, he offered the raw truth about what comes after the finish line—an aspect few discuss, especially in public.
Lessons for Entrepreneurs
Shankar’s story carries essential lessons for entrepreneurs at all stages. Building a successful company requires intense commitment, but founders must also prepare for life beyond the business. Emotional resilience, a diversified identity, and a broader sense of purpose can help cushion the blow of an eventual exit.
The notion that financial success equates to emotional fulfillment proves dangerously misleading. While money offers freedom and security, it cannot replace meaning or personal connection. Shankar’s story challenges the startup community to rethink how they define success and to prepare mentally for what happens after the win.
He didn’t let the void consume him. Instead, he took steps to reinvent his path. But he wants others to know that this reinvention doesn’t happen automatically. It demands reflection, patience, and the courage to start anew.
Redefining the Narrative
Siddharth Shankar’s journey illustrates that success is more complex than a headline figure. Selling a company for $500 million might look like the ultimate achievement, but the human story behind it tells a different tale.
The emotional fallout, the loss of structure, and the fight to rediscover purpose form a narrative few talk about. By speaking openly, Shankar not only lifts the curtain on post-exit life but also redefines what it means to succeed.
He didn’t just build a company—he built a life around it. And when that life changed, he faced the challenge of rebuilding from the inside out.
In sharing his story, Shankar reminds us that entrepreneurship is not just about ambition and hustle—it’s also about meaning, identity, and human resilience.