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This conversation is a powerful reminder that entrepreneurs must consciously evolve from being hands-on operators to becoming true leaders. In the early stages, control feels necessary. Every decision, review, and execution flows through the founder. But scale, sustainability, and sanity only come when the entrepreneur shifts focus to building systems, senior leadership, culture, and reputation. Ankita Gupta’s journey as founder of Digitactix shows that leadership maturity is less about doing more and more about enabling others to lead, while anchoring the organization in values and long-term vision.

Ankita shares her entrepreneurial journey - from intentionally stepping out of her comfort zone to building a values-first agency focused on ROI, transparency, and long-term reputation. She reflects on balancing health, family, and leadership; navigating entrepreneurship as a woman in India; and how experiences like Harvard Business School’s OPM and YPO reshaped her perspective on leadership, culture, and systems. The conversation emphasizes evolving leadership, ethical decision-making, self-awareness, and building institutions that outlast the founder.

Here are the Top 10 Takeaways from the conversation:

1. Growth begins outside the comfort zone: Digitactix was born from Ankita’s desire to challenge herself, not from a rigid business plan.
2. Health is foundational to leadership: “If I’m not fit, I cannot run a fit organization.” Fitness is a lifelong investment, not a short-term goal.
3. Entrepreneurship requires support systems: Family support played a critical role in enabling her to build the business while raising children.
4. Shift from operator to institution builder: OPM helped Ankita move from micromanaging everything to building senior leadership and systems.
5. Transparency is a competitive advantage: Ethical practices, honesty about ROI, and refusing misaligned clients built long-term trust and reputation.
6. Values over vanity metrics: Real success lies in ROI, ownership, and impact, not superficial growth numbers or agency rankings.
7. Reputation compounds over time: Clients returning after trying other agencies validated the long-term value of principled execution.
8. Culture drives sustainable success: Leadership, systems, and culture come first; growth and finance follow as consequences.
9. Safe peer communities reduce isolation: YPO provided a judgment-free space to discuss failures, emotions, and real struggles of entrepreneurship.
10. Wisdom is self-awareness: In an AI-driven world where skills evolve rapidly, knowing your strengths, weaknesses, and blind spots matters most.

Books: Good to Great