How Being Underestimated Drives Success In Business

Have you ever had a great business idea that you were so excited to share, only to be met with a wave of reasons why it wouldn’t work? The budget’s too tight. You’re too green. The market isn’t ready. The subtext is often louder than the critique.

Every successful person has once been underestimated. At first, it may seem like a liability, but in reality, it’s a valuable leverage in the right situations. Yet the harshest critic is often the one in the mirror.

A Workera study revealed that more than half of its users (56%) tend to undervalue their own abilities, while 32% rate themselves higher than their actual skill level. Only 11% accurately gauged their standing. Even with a wider margin for error, underestimation remains the dominant bias.

Once you can manage your own thoughts, it’s easier to deal with people who consider you an underdog.

Thai Randolph understands this all too well. As a seasoned media executive and multi-hyphenate, well known for her involvement in building and scaling Kevin Hart’s media company, she’s walked into rooms where her goals were too steep and her confidence too bold. But instead of shrinking to fit expectations, she stayed the course.

For Randolph, rejection didn’t end the story; it rewrote the rules as she leaned in.

Rejection Isn’t the End. It’s The Starting Line

Early in her career, Randolph sought advice from a respected family friend she admired, someone who could open doors. But instead of encouragement, she was met with tempered expectations. The message was clear: be more realistic, tone it down and wait your turn.

“I was crushed,” Randolph recalled. “But simultaneously, it ignited something pretty powerful within me.”

Randolph reassessed how she was telling her story. She walked away from three “perfectly good” job offers that didn’t align with her goal. She stuck to her vision and eventually landed one that exceeded even her own expectations.

Her philosophy centers on what she calls F.U.E.L: feel it, use it, execute it and let the results do the talking.

Turn Underdog Energy Into Firepower

As the former CEO of Hartbeat, she led the merger of Hartbeat Productions and Laugh Out Loud into a $650 million global entertainment powerhouse. She secured $100 million in growth capital—marking one of the largest raises by a Black woman.

She didn’t rise the ranks by letting the underdog persona stop her. She used the negativity as a source of raw energy to channel it into something productive.

“That same negative energy can be transformed into that fire inside you that burns you,” Randolph comments. “If you look at any modern hero of art and business, they often have these moments where it was, ‘I was rejected X number of times’ or ‘I had this shocking betrayal; a shocking disappointment’ ‘I lost it all to gain it back.’ That conversion mechanism, when you can say, ‘Look, I’m going to take this, use it as energy; I’m going to use it as fuel to power. What’s next?’”

Build With Purpose And A Bigger Why

Randolph grounds her ambition in something larger than personal gain: economic justice. She sees women and communities of color not just as underserved but as underleveraged powerhouses.

“Women control trillions in consumer spending, yet capital and representation haven’t caught up,” she said. “That’s a huge motivator.”

For women, especially women of color, the road to leadership often comes with more detours and more criticism. Feedback is constant, but not all of it is useful. As Randolph puts it, “Take what sharpens your strategy and leave the rest.” The ability to discern which advice helps you move forward and which reflects someone else’s limitations is key to staying aligned with your own goals.

Too often, well-meaning mentors project limitations. Randolph suggests a better approach by speaking first to a person’s potential and then offering guidance.

“Every person, at any moment, possesses unlimited capacity,” she concludes. “Just because a path worked for you doesn’t mean it’s the playbook for someone else.”