I was a small part of a big team that brought Dragons' Den, the Canadian version of Shark Tank, to life. O'Leary played a much bigger part in making that show a huge success--so much so that his Dragons' Den appearances earned him an invitation down from great white north of Canada to star in the American version.the
Most people see O'Leary's sharp tongue and sharper mind weekly and believe that to be the true Kevin O'Leary. They see a heartless capitalist only focused on one thing: profit. But having watched the man up close for a prolonged period, I think that one-dimensional summary does him a disservice.
As an entrepreneur, you're required to unequivocally believe your own hype. It's your Achilles heel--your confirmatory biases both allow you to persevere and blind you to some cold, hard truths.
I believe O'Leary cares, and cares deeply, for the entrepreneurs seeking his investment. I believe he genuinely wants his acrimonious advice to spur the entrepreneurs before him (and the millions of "wantrepreneurs" watching on television) to think more deeply and more honestly on the opportunity.
He and I have spent a lot of time together. O'Leary even wrote the foreword for my book. Here are five O'Leary quotes that support my case--and while they're all from Shark Tank, I've heard him say near-identical things in person.
1. "It pains me to see good entrepreneurs chase bad opportunities."
This is basically O'Leary saying your idea isn't worth your time. You often hear this advice if the opportunity you're pursuing is small.
He's right: Most ideas aren't worth the risk. How do you find an opportunity where the reward justifies the risk? Focus on the basics: a big and growing market; huge, expensive incumbent solutions based on archaic technologies; and accessible early adopters with inelastic, unmet market needs.
2. "Whatever you pay attention to grows!"
Here, O'Leary is begging you to focus on your value proposition: that is, how you solve unmet market needs exponentially better than everyone else.
It's easy to get distracted by vanity metrics--numbers that make you look good to outsiders but don't help inform your business strategy--but those won't generate profit.
Key performance indicators (KPIs) are the opposite. These are the numbers that inform action. For Facebook, a KPI might be engagement: an average day-over-day increase or decrease in the time spent online by user.
Focus on KPIs that show trends, not individual data points--month over month, week over week, or day over day. Pay attention to the unit economics that inform you about your company's health trends. For Walmart, for example, that might be the monthly increase in average revenue per square foot of store. For a hotel, it might be month-over-month occupancy rates. It's the extra revenue you get for each unit you sell.
3. "I like to take risks. That's how I make money. But they are calculated risks."
Good entrepreneurs aren't highly risk-tolerant. That's a stereotype. Entrepreneurs are simply better assessors of key risks.
The best and least-used method to lower risk, in my opinion, is customer discovery. It's a face-to-face process in which you engage directly with early adopters to ask questions and confirm your assumptions about their unmet market needs.
You should hear from real people before you make products for them. It'll dramatically decrease the risk that you're building a solution nobody will pay for.
4. "Nobody has a monopoly on good ideas."
This is my favorite. O'Leary uses it often, usually when entrepreneurs are pitching nothing but ideas. He knows, as do I, that action drives entrepreneurship. Execution is what drives value.
If you come to investors with only an idea, you'll get nowhere. You'll probably need to create early sales or other forms of traction before pitching investors. One of the easiest ways to do this is through crowdfunding; selling 100,000 units in advance of building the product is exponentially more powerful to pitch investors.
5. "My partners...taught me that in order to create wealth, I needed to pair up with people whose strengths compensated for my weaknesses."
It's hard to admit that your management team is missing a key element. Most startups need a talent triangle: founders with equal parts domain knowledge, business acumen, and operational know-how.
Unfortunately, few entrepreneurs going in to pitch someone like O'Leary meet those requirements. This can be addressed. Personally, I recommend co-founder matchmaking platforms like Founder Dating and CoFoundersLab.
I spent five seasons behind the scenes on Dragons' Den and I never met an entrepreneur who didn't think they'd be the best thing the investors had ever seen. Reading these quotes should offer you a valuable, classic O'Leary perspective: one of unbiased honesty.
Use that gift well.