Success Advice
10 Brutally Honest Success Lessons from Kevin O’Leary of Shark Tank
Kevin O’Leary is a Canadian born entrepreneur and TV personality who rose to prominence in the business world after his software company sold to Mattel for $3.65 Billion in 1999. He is best known for his no-nonsense and often blunt criticism of aspiring entrepreneurs and startups on ABC’s Shark Tank.
Also known as “Mr. Wonderful”, Kevin O’Leary has since written 3 best selling books about life, entrepreneurship, and money; and what it really takes to make it in the big leagues of business.
Here are 10 success lessons you can learn from Kevin O’Leary:
1. Business is war
An entrepreneur should be in it to win it – to crush the competition. Kevin has a no nonsense approach to business which is void of emotion. Business is war, and you have to play to win. Don’t let your feelings get in the way. The market will determine who survives and who doesn’t, so play the game with everything you’ve got. Don’t be afraid to lose. Just reassemble your troops and try again with a different strategy.
“Business is war. I go out there, I want to kill the competitors. I want to make their lives miserable. I want to steal their market share. I want them to fear me and I want everyone on my team thinking we’re going to win.” – Kevin O’Leary
2. Your dollars are your soldiers
Money is the lifeblood of business. Many will espouse how money is over rated, and shouldn’t be the most important pursuit of business. Kevin disagrees. He likens your start up finances to your soldiers on the battlefield of business. “Here’s how I think of my money – as soldiers – I send them out to war everyday. I want them to take prisoners and come home, so there’s more of them.” If some of them die, that’s bad. If they all die, that means you’re broke.
3. Entrepreneurship = Freedom
Kevin tells a story of when he was a teenager and worked at an ice-cream store in a local mall. One day he was asked to scrape gum off the floor, and when he refused to, was fired. Reflecting on this years later he says that it taught him that being an employee is slavery and being an entrepreneur is true freedom. From that day forward he vowed that he was never going to work for anyone else again.
4. Spend the interest, never the principle
As the chairman of O’Leary funds, Kevin’s entire investment firm is based on this fundamental lesson he learned from his mother at an early age. His mother would always say “Spend only the interest, never the principle.” This means don’t let go of your nest egg. Leave the principle alone to accumulate interest, and send that interest back out into the battle field.
5. Don’t fall in love with bad ideas
Money runs from bad ideas. Entrepreneurs who are in love with bad ideas kill companies and send money running. On Shark Tank, you will often see incredibly passionate entrepreneurs who are infatuated with terrible ideas that either don’t sell or aren’t backed by viable business models. Kevin is quick to bring a dose of reality. “I have met many entrepreneurs who have the passion and even the work ethic to succeed – but who are so obsessed with an idea that they don’t see its obvious flaws. Think about that. If you can’t even acknowledge your failures, how can you cut the rope and move on?”
6. Opportunity comes fast
Known for saying “opportunity knocked, nobody was home”, Kevin shows entrepreneurs on Shark Tank that opportunity comes fast. It also leaves just as quickly. An offer from an investor can arise and expire in moments. You need to think fast, and make quick decisions under pressure.
7. Passion isn’t everything
Kevin started out wanting to be a fashion photographer until his father shot down that idea with some brutal honesty. “You’re just not that good.” his father told him. Kevin realized that to make the kind of money that he wanted to make, his passion of photography just wasn’t going to get him there. He wasn’t prepared to be a starving artist with most of his photos going unsold, so he left his passion behind to pursue business. Don’t let your passions blind you and lead you away from success.
8. Sales are everything
Many otherwise viable business ideas and startup companies have been harshly rejected in the Shark Tank because they simply have no sales. Sales are everything. You could have the greatest idea in the world with a plan to execute, but if you approach an investor with no sales or tangible purchase orders you will be in for a tough sell. Investors want to see real market demand with real paying customers before they will back ventures. They don’t want to back speculation without actual sales which will confirm that your business model works.
“Do you have what it takes to make the sale?” – Kevin O’Leary
9. Money doesn’t care about you
Kevin once said “Don’t cry about money, it never cries for you.” The lesson here is to keep your emotions separate from your money. Never let your emotions dictate what you do with your cash, especially if you are in the early stages of a start up. If you are losing money, the market is trying to tell you something. Change your model or get out of that business – but don’t cry about it.
10. The price of success is high
“Working 24 hours a day isn’t enough anymore. You have to be willing to sacrifice everything to be successful, including your personal life, your family life, maybe more. If people think it’s any less, they’re wrong, and they will fail.” Kevin is not a believer in the life work balance. There is no balance. You must be willing to give everything to be successful. It is this kind of hardcore work ethic that separates those who fail from those who succeed on a big level.
What do you like most about Kevin O’Leary? Please leave your thoughts in the comment section below!
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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.
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