Kevin O’Leary, venture capitalist, entrepreneur, and investor, shows that common sense and instinct combined with embracing AI is businesses’ best bet.
As someone who invests in scaling businesses, how do you evaluate whether a company is truly investing in its people — especially when it comes to upskilling or reskilling in the AI era?
AI is very nascent, but it’s proving to provide some interesting productivity in all 11 sectors of the economy, which is remarkable and may be more impactful than the Internet was in terms of making companies more efficient.
My first question, is how are you using AI to reduce customer acquisition cost and customer maintenance? That’s where the growth is. And if you don’t even have anybody running social media or developing content, and you’re not using AI, I know who your competitor is: It’s the companies that are now adopting use of social media and using AI to generate the content on the social media and analyze [that] and watch what the market is doing using AI.
How do you see the role of HR evolving as more decisions from hiring to engagement are driven by data and AI?
Right now, for example, we are contemplating hiring a new CEO for a new venture. I said, “Would you consider becoming a contractor for six months as opposed to a fully empowered employee, and we’ll pay you 30% more than your base contracts. No stock options, no benefits for this six-month period. But wouldn’t you like to test us first? And we’d like to road test you to see if you integrate with the existing team you’re working with and you’re about to lead and the operating company above you that controls the company. Don’t you want that experience?”
What’s the biggest mistake leaders make when trying to build culture in remote or hybrid teams and what works?
The key to hybrid teams and remote teams is moving from micromanagement to project-based management. You set goals on a weekly, monthly, or quarterly basis. You don’t care when the employee works. What you care is if they hit the target on the project-based goal. You’re not a project-based employee if you strike out three times. You need to be in a cubicle in a basement somewhere.
If you were building a company from scratch in 2025, how would you approach employee experience from benefits to internal mobility?
We have quarterly meetings. And during the winter we do them in Miami Beach. We spend three days together getting to know each other and talking about our goals for the next quarter. But at the end of the day, we do use a weekly all-hands call for 30 minutes all around the world. We make sure we look at each other for 30 minutes. No matter where you are, you’re going to be on that call. That way we the culture remains intact.
How should HR leaders today think about ROI when investing in technology like DEI tools, wellness benefits, or people analytics?
You have to set goals. The longest I will tolerate losses is 36 months. If you haven’t figured out the business model in three years, CAC and ROAS, customer acquisition, cost, return on ad spend, whatever it is in any sector, then you don’t have a business.
