Dream Big, Iterate Fast with Medha Agarwal

“No one works as hard as founders do. They’re operating on another level of intensity.” - Medha Agarwal

Is your pitch holding you back more than your business idea? Are you making it easy for investors to dream the dream with you? In this episode, I sit down with Medha Agarwal, General Partner at Defy, to talk about the unique challenges founders face—especially women—when pitching their startups, securing funding, and leading through growth. She shares why too many founders unknowingly undersell their vision and how simple shifts in storytelling can make all the difference.

Medha also opens up about her own career journey, from being a founder to working in venture capital, and what she’s learned about choosing the right team, adapting in fast-moving startups, and pushing past perceived limits. We also dive into her experience as a Harvard rower and the powerful leadership lessons she’s carried from the water to the boardroom.

Whether you're a founder, thinking about launching a startup, or simply curious about what separates the best pitches from the rest, this conversation is packed with actionable insights on confidence, resilience, and strategic growth.

You'll hear us discuss:

• Why women founders struggle with selling the big picture – Medha explains that many female founders naturally emphasize what still needs to be done rather than what they’ve already achieved. Investors need to see the vision and the opportunity, not just the challenges ahead.
• The subtle shift that makes a pitch stronger – Instead of pointing out gaps or weaknesses, founders should frame their journey as momentum. Investors want to be inspired—help them see how they can be part of something big and inevitable.
• The underestimated importance of flexibility in startups – Too often, people transitioning from corporate jobs to startups focus on titles and initial responsibilities. But in a fast-growing company, your job will change drastically every six months. The real key to success is choosing the right company and founder rather than clinging to a specific role.
• What makes a startup worth joining – Medha stresses that it's better to join a company where you believe in the founder’s vision and leadership style, even if the role isn’t perfect. A rising tide lifts all boats—if the company succeeds, so will your career.
• How rowing taught her to lead and collaborate – Rowing is the ultimate team sport, where trying to stand out individually slows the whole boat down. The same applies in startups—success comes from alignment, trust, and moving in sync with the team.
• The reason she prefers working behind the scenes – Medha admits she’s uncomfortable with the spotlight on herself and much prefers helping others shine. This mindset makes her a stronger investor and advisor—she’s fully focused on helping founders succeed, not chasing personal recognition.

Resources

Medha Agarwal on LinkedIn | Defy

Winnie da Silva on LinkedIn | On the Web | Substack | Email - winnie@winnifred.org