Entrepreneurs
5 Reasons Why Underdog Entrepreneurs Are More Likely to Succeed

The world is in a place right now where everything is changing faster than ever. Thanks to the digital era, we are enabled to fulfil our dreams easily. Be it the flexible policies or the availability of easy information, it all allows us to work more effectively towards our goals. It’s the same for entrepreneurs alike.
Not everyone is cut out to be an entrepreneur though, that’s mean but true. However, there are many more entrepreneurs today than there was just a decade ago. How is this happening?
People without entrepreneurial backgrounds are trying their luck and succeeding too. It’s a good wave for everyone, the consumer and the seller. The market is working together to reduce the gap between demand and supply. Not only is this keeping entrepreneurs on their toes, but is also encouraging them to think out of the box.
This sudden rise in the number of entrepreneurs could also be attributed to the availability of investors. They most certainly think differently than their predecessors. The desire to bring in the right change in society is the only thing similar between all generations of entrepreneurs.
Who is an underdog entrepreneur?
Underdog, as the term suggests, is someone who is least expected to succeed within a group of talented individuals. It is the same person who has the least power, say or authority in the lot. Underdogs are never usually even considered to be on the winning side. This in return makes it obvious for others to not have any hopes on them or worse, not even consider them. Some could argue that underdogs are usually not visible to others.
“Being underestimated is one of the biggest competitive advantages you can have. Embrace it.”
However, over the years the above definition is seen in a more positive and different light. Underdogs are highly respected and regarded now, because of the uncertainty they carry with them. It reflects on the idea of someone weak or slow, working harder to be in a better position. Underdogs look appealing today because of their efficiency at breaking odds and coming out stronger. Today, underdogs also answer to the injustice or unfairness they are fighting to succeed.
Here are 5 reasons why underdog entrepreneurs are more likely to succeed:
1. They don’t take any aspect of their business for granted
Underdog entrepreneurs are from humbler backgrounds in terms of experience making them sceptical. They take every aspect of their business seriously. Be it something as small as managing their accounts or something as big as meeting an investor, they do it with equal determination. There are times when big businesses face trouble for having taken a small aspect lightly. This is usually never the case with an underdog entrepreneur, who is always on his toes. He is careful and is alert about what’s happening in and outside his business. This keeps him aware and also allows him to plan ahead in time.
2. Their risk tolerance is out of the world
They have faced failures multiple times in the past. They do not have inhibitions and scepticism, unlike most entrepreneurs. Taking calculated risks is a wise choice but can also keep one back in today’s fast marketplace. Underdog entrepreneurs are usually more likely to take risks that others are not willing to take. This certainly puts them in a tricky position but also improves their chances significantly. They understand the risk they are taking and take it with authority. They are the same type of individuals who believe they have nothing to lose in the first place. They risk it with the hope of getting something better. Even if they fail they know how to rise up again. Staying motivated even in the toughest of times is an art they have nailed.
3. They don’t make unnecessary chatter or claims
Underdog Entrepreneurs usually have too much on their plates; given the multiple hats, they wear. They don’t have the time or flexibility to indulge in useless banter. There are two kinds of people; doers and talkers. They are the first kind, who focus on doing things better. Their words speak for them. Having faced rejection and failure, they are usually very cautious before making any claims. They take failure positively but also learn not to talk about outcomes that aren’t out yet. These are the category of people who let their work speak about them. Underdog entrepreneurs are usually never satisfied and try to make up for the lost time and repute.
4. They think out of the box and have unconventional ways
They are the kind of people who experiment and run wild thoughts. Their fearlessness makes them take calculated yet unconventional steps. It could be in their execution or their promotions etc. The world is changing and is craving to see the right change. Unlike earlier times, the ideal consumer today is more willing and open to the right changes.
However, the consumer wants to know the logical reason behind a change. Underdog entrepreneurs are making better decisions every day and coming up with quirky ideas too. This is the time and age for unconventional settings and decisions and underdog entrepreneurs are making the best out of it. Their experience at falling and getting back up each time teaches them how to find better ways to rise up.
“Underdogs adapt, evolve and become winners because of their preparation, heart, execution and the relentless attitude that the game will not end any other way.”
5. They have exceptional people skills
It’s very important for every business to connect with its people, its consumers. The unique bonds that brands are creating today, is what separates them in the crowded marketplace. Coming from humble beginnings, underdog entrepreneurs are humble and open-minded. They talk to people, connect with them, share and take ideas. Underdog entrepreneurs shine at creating relationships that matter to their business.
They understand that there are many others like them in the market and keep their ego in check. They are more respectful of their customers and towards their competitors. This keeps them open to new learning, which should ideally be the motto of every entrepreneur. This is the same ability that makes them better advisors, mentors, leaders and salesperson. They understand human emotions and values better.
When an underdog entrepreneur finds success, he/she makes others believe in the power of hard work and determination. This is the positivity that people look out for in the first place.
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
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Build diverse talent pipelines
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Embrace flexible work models
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
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History shows us that the greatest minds, Albert Einstein, Thomas Edison, Oprah Winfrey, Michael Jordan, Walt Disney, Stephen King, and countless others, faced failure early on. Yet, instead of seeing failure as the end, they treated it as a comma in their story, not a full stop. (more…)
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