This Guy Almost Became CEO Of Apple, Google, And Yahoo - Here's What It Feels Like To Miss Out On Big Opportunities

Not a lot of people get to have the type of experience Joe Costello's had through his long career.

Before Costello was the CEO of Enlighted, a connected lighting network startup that's raised $55 million so far, he was a much bigger figure in tech.

He was the CEO of Cadence Design Systems, a design and engineering software company, for nearly a decade in the 90s, until 1997. Cadence currently has over 5,700 employees and a market cap over $5 billion.

Most recently, he was the CEO of Orb Networks, a media streaming hardware startup, that was sold to Qualcomm last year. He was also named the top CEO of America back in 1997 by Chief Executive Magazine.

So it's pretty safe to say that Costello's had a successful career - that is, only if you don't count all the missed opportunities he's had along the way.

In 1997, shortly after he left Cadence, Apple's then-acting CEO Steve Jobs called him for an interview. The two talked for a few hours, but their conversation only led to Jobs realizing he himself actually wanted to be the full-time Apple CEO.

After that, Costello joined an education startup called Knowledge Universe, which was backed by Michael Milken, the infamous "junk bond king," and Oracle's Larry Ellison. That gig didn't last too long, as he left after three months over management issues.

In 2000, Google's Larry Page and Sergey Brin interviewed Costello for the Google CEO job that eventually went to Eric Schmidt. But right around then, Costello had already agreed to join a startup called Think3, and was deeply involved in their fundraising process.

"[Google] was a really cool company, but I had made a commitment to this other thing, and I had to honor that commitment," Costello recalls to Business Insider.

Fast forward a few years and Costello had another shot at a big tech company. This time, it was Yahoo. He had an interview with Yahoo cofounder Jerry Yang and Sequoia Capital's Mike Moritz. But Yahoo at the time was making a shift to a media company, and decided to go with Warner Brother's Terry Semel instead.

When asked if he had any regrets over all of this, especially his decision to pass on Google, Costello put it simply: No.

Why? "Because it wasn't a decision I agonized about," he says.

"If you make a commitment to someone, you have to follow through on it," Costello says. "Obviously, it would have been a cool thing and probably would have made me a lot more money, if I had joined Google. But you've got to make choices that feel right to you, and honor all your principles."

He continued, "Looking at my history, you might say because I didn't take that Google position, I made the biggest professional mistake in technology. But the beauty of this, or anybody in tech, is there's not just one opportunity."

"It's a great industry filled with these incredible technologies that help people across all kinds of disciplines. Everybody's going to have those down times. Just look forward and look for all the cool opportunities, and I guarantee, within days, you'll be rocking and rolling again."

For Costello, now 60, that new opportunity is in the Internet of Things industry, where his current company, Enlighted, is making a lot of noise.

Enlighted's sensor technology lets a commercial building track how people use its offices. For example, the Enlighted system can monitor what rooms are empty or most frequently used, and control the lights and air conditioning of that specific space accordingly. With the data it collects, it also maps out how to use office space more efficiently.

Companies that use Enlighted's technology now save 50 to 75% of their energy costs, according to the company. Its system now covers more than 10 million square feet of commercial real state, and their long list of clients include Google, Linkedin, and HP.

Costello estimates the IoT business for the commercial space alone could be worth billions of dollars.

"This is the single largest market opportunity that I've ever gotten close to," Costello said. "This market is just enormous and we're growing exponentially."

Here's a video of how their technology works: