Investment guru regrets not buying this company the most

Ever look at stocks and wonder how people decide what to buy and when?

Greycroft Chairman Emeritus Alan Patricof is considered by some to be the founding father of venture capital, as he was an early investor in companies like Apple, AOL and Office Depot.

Patricof joined FOX Business' Liz Claman on "The Claman Countdown" on Thursday to share many of his investing tips as well as what he regrets not buying when he had the chance.

What he looks for when investing

Patricof told FOX Business he first looks for who is running the company, how capable they are and what kind of team they have. He calls that person "the jockey."

"We found that the best kind of jockey is someone who did it before in a similar industry and then can attract people from his former company to join him, which means they're voting with their careers whereas we're just voting with our money," Patricof said.

He said once they determine the jockey and what product or service they're planning on providing, then they move onto the economics of the business.

Patricof said they ask themselves if the economics work and make sense. If they do, then it's a formula for profitability.

What makes a good venture capitalist?

Patricof said it's important for a good venture capitalist to pay attention to numbers and to what the company is doing.

"They ask the right questions and [try] to impose from a director's role only not in an operating role — the right conditions and does question its steps that are being taken in and along the way," he said.

Patricof mentioned the current WeWork IPO issues as an example.

He said when he first spoke with WeWork CEO Adam Neumann and visited the facilities, he thought it was a "very exciting concept" and thought it was "the future of retailing." They weren't fundraising at the time for the company.

But, he said what Neumann did in terms of building the company and where it ended up is a whole different story. He said if he had been on the board, he would have questioned some financial decisions being made by WeWork. However, Patricof said since Neumann had a supermajority of the stock and had chosen the board members, that didn't seem to happen.

"They were all seeing the pot at the end of the rainbow" instead of being scrutinous, Patricof said.

What's the most exciting investment of 2020?

Patricof recently committed a lot of money to The RealReal, which is an online marketplace for luxury consignment goods. He also was an earlier backer of Venmo, which is now owned by PayPal. But what's on his horizon?

"We just closed the deal with a company called LEX which is a new concept of a real-estate equivalent of, let's say, Nasdaq where you could buy and sell minority interests or small interests, less than majority interest, in real estate, and that is going to be qualified for non-accredited investors," Patricof said.

He also said he's done a number of investments in the podcast arena, especially the company Wondery which produced popular podcasts like "Dr. Death" and "Dirty John," as well as a company called Podsights which does ad attributions for podcasts.

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He also mentioned investing in Glow, which offers subscriptions for podcasters as well as Chartable which helps podcasts market products.

What was the stock that got away?

Patricof joked he always says the same answer: Starbucks.

He said when he first heard the concept of a new concept of a coffee shop, he said "In New York, we have coffee shop[s] ... on every street, and it's certainly on every corner. What in the world do we need a new coffee shop?"

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He said he was being too petty and didn't realize the concept was closer to a space where people could socialize while drinking coffee instead of the luncheonette countertop place he was picturing.