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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9 Harsh Truths Every Young Man Must Face to Succeed in the Modern World
Before chasing success, every young man needs to face these 9 brutal realities shaping masculinity in the modern world.
Many young men today quietly battle depression, loneliness, and a sense of confusion about who they’re meant to be.
Some blame the lack of deep friendships or romantic relationships. Others feel lost in a digital world that often labels traditional masculinity as “toxic.”
But the truth is this: becoming a man in the modern age takes more than just surviving. It takes resilience, direction, and a willingness to grow even when no one’s watching.
Success doesn’t arrive by accident or luck. It’s built on discipline, sacrifice, and consistency.
Here are 9 harsh truths every young man should know if he wants to thrive, not just survive, in the digital age.
1. Never Use Your Illness as an Excuse
As Dr. Jordan B. Peterson often says, successful people don’t complain; they act.
Your illness, hardship, or struggle shouldn’t define your limits; it should define your motivation. Rest when you must, but always get back up and keep building your dreams. Motivation doesn’t appear magically. It comes after you take action.
Here are five key lessons I’ve learned from Dr. Peterson:
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Learn to write clearly; clarity of thought makes you dangerous.
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Read quality literature in your free time.
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Nurture a strong relationship with your family.
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Share your ideas publicly; your voice matters.
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Become a “monster”, powerful, but disciplined enough to control it.
The best leaders and thinkers are grounded. They welcome criticism, adapt quickly, and keep moving forward no matter what.
2. You Can’t Please Everyone And That’s Okay
You don’t need a crowd of people to feel fulfilled. You need a few friends who genuinely accept you for who you are.
If your circle doesn’t bring out your best, it’s okay to walk away. Solitude can be a powerful teacher. It gives you space to understand what you truly want from life. Remember, successful men aren’t people-pleasers; they’re purpose-driven.
3. You Can Control the Process, Not the Outcome
Especially in creative work, writing, business, or content creation, you control effort, not results.
You might publish two articles a day, but you can’t dictate which one will go viral. Focus on mastery, not metrics. Many great writers toiled for years in obscurity before anyone noticed them. Rejection, criticism, and indifference are all part of the path.
The best creators focus on storytelling, not applause.
4. Rejection Is Never Personal
Rejection doesn’t mean you’re unworthy. It simply means your offer, idea, or timing didn’t align.
Every successful person has faced rejection repeatedly. What separates them is persistence and perspective. They see rejection as feedback, not failure. The faster you learn that truth, the faster you’ll grow.
5. Women Value Comfort and Security
Understanding women requires maturity and empathy.
Through books, lectures, and personal growth, I’ve learned that most women desire a man who is grounded, intelligent, confident, emotionally stable, and consistent. Some want humor, others intellect, but nearly all want to feel safe and supported.
Instead of chasing attention, work on self-improvement. Build competence and confidence, and the rest will follow naturally.
6. There’s No Such Thing as Failure, Only Lessons
A powerful lesson from Neuro-Linguistic Programming: failure only exists when you stop trying.
Every mistake brings data. Every setback builds wisdom. The most successful men aren’t fearless. They’ve simply learned to act despite fear.
Be proud of your scars. They’re proof you were brave enough to try.
7. Public Speaking Is an Art Form
Public speaking is one of the most valuable and underrated skills a man can master.
It’s not about perfection; it’s about connection. The best speakers tell stories, inspire confidence, and make people feel seen. They research deeply, speak honestly, and practice relentlessly.
If you can speak well, you can lead, sell, teach, and inspire. Start small, practice at work, in class, or even in front of a mirror, and watch your confidence skyrocket.
8. Teaching Is Leadership in Disguise
Great teachers are not just knowledgeable. They’re brave, compassionate, and disciplined.
Teaching forces you to articulate what you know, and in doing so, you master it at a deeper level. Whether you’re mentoring a peer, leading a team, or sharing insights online, teaching refines your purpose.
Lifelong learners become lifelong leaders.
9. Study Human Nature to Achieve Your Dreams
One of the toughest lessons to accept: most people are self-interested.
That’s not cynicism, it’s human nature. Understanding this helps you navigate relationships, business, and communication more effectively.
Everyone has a darker side, but successful people learn to channel theirs productively into discipline, creativity, and drive.
Psychology isn’t just theory; it’s a toolkit. Learn how people think, act, and decide, and you’ll know how to lead them, influence them, and even understand yourself better.
Final Thoughts
The digital age offers endless opportunities, but only to those who are willing to take responsibility, confront discomfort, and keep improving.
Becoming a man today means embracing the hard truths most avoid.
Because at the end of the day, success isn’t about luck. It’s about who you become when life tests you the most.
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