Why Underdogs Make Better Leaders

As much as it sucks to feel like the underdog, outsider, or to feel like the imposter in the room… it’s one of the biggest advantages you'll have as a leader.

When I started at my first seed-stage startup, I was a liberal-arts-kid / pro singer and actor, hired into customer support without any clue what I was doing.

Years later, after lots of accomplishments, awards, promotions, and leading teams—I still felt like an idiot half the time.

That experience in high growth companies defined the way I began to lead, and I’ve come to think of this as underdog leadership —low-ego, high questioning, people-first leadership, and practical, shaped by humility, curiosity, and lived experience vs. pedigree.

Growth stage, I was promoted to Director of Operations at Seamless, reporting to the CEO and surrounded by Ivy Leaguers and ex-consultants u admired, asking myself, “why me?”… “did they make a mistake?”…”when will they figure it out?”.

Here's the thing….

Overconfidence is difficult to unlearn - it's an obstacle to growth, but confidence can be built. Humility often can’t, especially once people are in positions of power--and once you get there, you need to work extra hard to stay grounded, and surround yourself w/people who challenge you. This is why low-ego leadership outperforms high-ego leadership in high-growth environments. When we’re too confident, we shut things down. In practice, underdog leadership produces stronger teams, faster learning cycles, and higher trust in fast-growing organizations.

Low confidence makes you a better learner - it pushes you to ask questions, gather context, check your thinking, seek to understand. Curiosity keeps you honest and in integrity - feeling like you don’t know enough might feel awful in the moment, but it’s keeps you aligned with reality, with multiple POVs vs. assumptions.

Underdogs and low ego folx can connect with people at all levels - they're less hierarchical, and they're not in a tower looking down on others. When you’ve been the junior, outsider, or only, you lead with empathy. People trust you faster. I see this most often in startup operators, first-time executives, and leaders scaling teams for the first time.

Humility as a leader is critical. If you embrace this part of you more, you’ll build the leadership muscles that actually matter, and set yourself apart in an age of disconnection, high technical expertise, and AI, where soft skills and EQ are a differentiator.