Skip To Main Content
July 6, 2021 - By Barron Rosborough

Mr. Wonderful Shares the 3 Key Components to Great Startup Pitches with Hawke Media

Kevin O’Leary is known for his role as the shrewd investor “Mr. Wonderful” on ABC’s hit series, Shark Tank, where hopeful entrepreneurs pitch their businesses for a chance to secure capital from Kevin and a panel of investors. Now, Kevin is bringing that pitching experience directly to the public.

Kevin O’Leary has joined forces with my FinTech partner StartEngine — the largest equity crowdfunding platform in the U.S. that has raised over $350M for hundreds of startups from thousands of everyday investors. Alongside Hawke Media and a number of known sponsors, Mr. Wonderful and StartEngine host a new pitch competition open to all founders ready to take their turn at pitching this shark.

Five finalists will pitch Mr. O’Leary live for a shot to hear what he thinks of their business, and the winner will receive a grant of $25K and over $40K worth of in-kind services from the sponsors. Founders can submit pitch applications at .

As one of the world’s most interesting investors with the larger-than-life persona to back it up, I took some time to chat with Mr. Wonderful about his roots as an entrepreneur and his advice for people trying to start a business.

Let’s start at the beginning. How did you become an entrepreneur? From what I’ve read, it seems like you’ve had it in you from a very young age.

I’ve had the drive to be an entrepreneur ever since I was a teenager. I got fired once, from a job at an ice cream parlor, and I knew then and there that I never wanted to have a boss again. I wanted to set my own priorities.

Why do you believe it’s so important to be honest with entrepreneurs about their business plans? 

Being an entrepreneur is a long and lonely road. I’ve done it. It consumes your life, and I owe it to entrepreneurs to be honest with them. If I see a fundamental flaw in a business idea, I’m going to point out that flaw before an entrepreneur dedicates years of their life to something that won’t ultimately succeed. I think it’s more respectful to the entrepreneur than giving false praise and guiding them down the wrong path.

Have you ever had a time when one of your business ideas failed, and has it shaped the way you interact with other entrepreneurs? 

Absolutely. I think failure is a foundational experience for any entrepreneur. In fact, if an entrepreneur hasn’t failed, I often won’t invest in them. Experiencing failure is a powerful motivating factor. Many entrepreneurs need to feel the sting of failure, and without it, many entrepreneurs are naive about just how hard it is to build a successful business.

What are the qualities you look for in a business when you make an investment? What makes an investment stand out? 

I have seen thousands of startup pitches, and there are three components to a great pitch.

  1. The founder can describe the business in 90 seconds.
  2. The founder can prove they are the right one to execute the business model.
  3. They know their numbers, from their gross margins to the number of competitors on the market. If a pitch has those three things, then they’ve got my attention.

How do you decide when to build a new business, and what does a successful plan to do so look like? 

I think it’s important to keep in mind the problem you are trying to solve. If your business doesn’t help people by solving a problem for them, whether they know they have a problem or not, then you’ve got nothing. Once you know, or believe with conviction, that your business addresses a real need that people have, it’s time to build.

To that point, one of the most important things an entrepreneur to do is start selling and validate your idea. If you can sell your product or your service to 1,000 people, and reach a point of sales well after exhausting your list of friends and family, then you know you’re on to something, and it’s just a matter of figuring out how to scale.

How did you get involved with the StartEngine live pitch competition? 

I came across StartEngine last year just as we were entering lockdown, and I was drawn to the platform immediately. The idea that startups can raise funding directly from their constituents and their customers and bypass venture capital funding entirely is brilliant. I’ve been encouraging the companies in my portfolio to leverage equity crowdfunding, and I became StartEngine’s Strategic Advisor as well so I could have more exposure to this space.

Will you be just as tough during the live pitch competition as you are on Shark Tank? What can viewers expect? 

This pitch competition is a bit different and is closer to a lightning round than what I do on Shark Tank. On the show, they edit our conversation down into a few minutes, but in reality, we have quite a bit of time to learn about the idea and dig into the business. This pitch competition is just a few minutes per company, so you’ll be getting my gut reaction to these elevator pitches. StartEngine does a great job of bringing a lot of variety to the competition, so I never know what I’m going to get.

Do you have any other advice for entrepreneurs trying to make it out there right now, especially during this crazy year we’re having?

Change brings opportunity, and a lot has changed in the past year. I think today is a great time to start a business, but I also think it is a difficult time to raise funding, so entrepreneurs need to be particularly mindful of their runway and what debt they take on, if any.

Catch Kevin “Mr. Wonderful” O’Leary on the next installment of StartEngine’s Shark Pitch competition on July 7, 2021, 9am PT / 12 pm ET. All founders are welcome to apply to pitch by visiting .