6 Brilliant Lessons I Learned from Shark Tank’s Kevin O’Leary

Arman Assadi
Solopreneurship and the Freedom Lifestyle
4 min readJul 29, 2014

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In “real life”, he’s a lot like what you might expect: direct, confident, and sharp. I recently had the opportunity to attend a keynote speech by Kevin O’Leary, founder and star of ABC’s hit show, Shark Tank. The keynote was in San Diego, CA, at the annual Traffic and Conversion Summit event.

Kevin, or “Mr. Wonderful” as he’s called on Shark Tank, has great stage presence and enjoys the limelight. More than anything, it was the content that stood out most. The keynote’s focus was on investing and finance, but the message came down to a handful of brilliant life lessons.
I think you’ll enjoy these lessons. Take a look at six of them below.

Lesson 1: Shark Tank Is Successful for One Reason

One of the first things Kevin O’Leary talked about in his keynote was the history and story of Shark Tank. The show did not find success right away. It took time to develop a following and passionate audience, but eventually it did. Kevin attributes this to one single value (and I couldn’t be happier with it).

Shark Tank is successful because people believe in Freedom.

Freedom, Kevin says, is the most desirable thing in the world. It’s something we all want. Success, money, fame, etc. all come in a distant second to having true freedom. People believe freedom is possible by watching shows like Shark Tank. They become motivated to do amazing things with their lives because of it.

I created my website/blog for one reason: to share an ideal I call the Freedom Lifestyle.

Lesson 2: Money Equals Freedom

It’s a simple formula: Money = Freedom.

Kevin explained that you’ll lose if you pursue money for any reason other than freedom. Nothing else can drive a person like the desire for freedom. The entrepreneurs that are pursuing freedom will find success.

If you use your money to educate yourself on accumulating wealth through investing in assets, you’ll get there. How do you define freedom?

To me, freedom is the ability to do what you want, when you want, how you want.

Lesson 3: Forget about Work/Life Balance

If you’re a solopreneur or entrepreneur, forget about work/life balance. According to Kevin, you must sacrifice to achieve your goals and become successful. You must focus on the work. You must go into isolation at times as well, because this is how the real creativity comes about.

I agree wholeheartedly now, and I think you should take this one seriously. When I first became a solopreneur, I didn’t believe this at all. I sold myself on a naive dream of maintaining my existing lifestyle with no interruptions, as if I was still working at Google. I didn’t want to sacrifice anything, and that’s a big mistake.

If you want to grow, learn, and push through the obstacles — you must go all in.

Lesson 4: Strengths vs. Weaknesses

Knowing your weaknesses is your biggest strength. It’s important to know the areas where you are the most weak, but don’t worry about trying to strengthen them. Work on making your strengths stronger, and do work that allows you to focus on only that. Where there are gaps, you must find solutions.

Which leads to…

Lesson 5: You Need a Partner

If you are building a traditional startup company or venture, you need a partner. Kevin explained that your partner must be strong in the areas where you are weak. It’s important to take a partnership seriously. Most people gravitate toward someone like themselves and this is wrong. Your partner should have a different style, mindset, and skill set. Together, you complement each other’s skills and can grow faster.

As far as solopreneurship goes, partners aren’t part of the plan, but you should still look for people to fill the gaps. It’s better to have strategic and joint venture partners.

The best way to grow and scale as a solopreneur is to build a team. These team members should handle all the aspects of your business you shouldn’t be working on (your weaknesses). Your first step will be to get an assistant, and then expand from there.

Lesson 6: Your Competition Is the Enemy

This final lesson from Kevin O’Leary was the most entertaining and controversial one. In characteristic form, he explained passionately that your competitors must be crushed. Business is war, and if you are not the first to act and “burn down the barn”, they will come after yours.

Again, in traditional big business, this holds more true. But, in the world of online businesses and solopreneurship, befriending your competitors is a better approach. I support my competitors and in return they have helped me grow. Yours can do the same for you.

Conclusion

Kevin O’Leary’s message was inspiring, actionable, and heartfelt. His persona on TV comes off as playful, but also cold and unsympathetic. While money is his main driver, he seems to do it all for the freedom it buys him and his family.

I found it interesting (and reassuring) that he drew such a strong parallel between success and being driven by freedom. I agree strongly with many of his lessons, but also disagree with some. This is because of the differences between traditional entrepreneurship and solopreneurship (as I define it).

Whether you’re already a solopreneur or intend to become one soon, I recommend you reflect on these lessons. There is much wisdom and success behind these words.
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Which lesson was your favorite?

Photo credit: ABC Shark TankCC license

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Arman Assadi is founder and Chief Solopreneur at WhyILeftGoogle.com(WILG). Arman helps solopreneurs, entrepreneurs, and wantrepreneurs create more freedom and work more effectively.

Follow with him on Twitter: @armanassadi

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Arman Assadi
Solopreneurship and the Freedom Lifestyle

Solopreneur, writer, consultant, soccer player, and obsessive world traveler #selfdirectedliving #freedomlifestyle | @armanassadi