Part of the mystery of modern air travel is wondering who you’re going to wind up sitting next to and how annoying they’re going to be. There’s no telling what John Waldron thought when on a flight in 1999 he saw that his seat was next to a couple with an eight-month old child returning from vacation.

As often happens he began chatting with the father, Krishna Pendyala, who was seated next to him, and they talked about what each did. Pendyala explained that he vice chairman and chief technology officer of MediaSite, a video search and retrieval company he had helped found. Waldron mentioned that one of his clients was a former chairman of the FCC and asked if Pendyala would like to meet him. Much to his surprise, Waldron called about two weeks later to tell him he had set up a meeting with the client who agreed to join Pendyala’s advisory board.

Pendyala’s not na??ve enough to think that as a business owner who had already sold one successful company that he wasn’t a potential client for Waldron, “but I never felt like he was hitting me up,” he says.

Time went on and as the two continued to talk and share perspectives on their respective businesses, they found common interests and developed a friendship. One of Pendyala’s interests has long been mentoring and coaching and he recalls predicting to Waldron in one of their early conversations that the human side of the client would become as important to his business in the coming years as managing their wealth.

A short while later he accepted an offer to sell MediaSite to a company based in Madison, Wisconsin. After years of having been his own boss, he now found himself as an employee, commuting several days a week from Pittsburgh to Madison. By that time he had two children and felt that the strain it was putting on his family was too high a price to pay, but he wasn’t sure he could afford to quit the job.

He wanted to know what was the minimum amount of money he needed to make in order to maintain his standard of living. It turned out not to be a simple question. He went to the manager of his portfolio, but he

only managed money. He went to another advisor whose replies all had to do with retirement, not current income. He went to a wirehouse “advisor” and says he felt like he had walked onto a used car lot.

“Finally I said, ‘I know John [Waldron], let me ask him.’ He said, ‘we do that all the time. That’s basically called cash flow-based planning.’ So they did a 20-year cash flow to answer the question, ‘what is the minimum amount that I need?’ Apparently, rarely does somebody ask that. It’s usually, “how can you grow, how can you do this, how can you do that?’” So what they prepared told me, ‘okay, you can quit that firm.’

This was the second time Waldron had solved a problem for him that other professional that he was paying had been unable to address. (The first time was when he was drawing up his will and his wife was not yet a U.S. citizen.) And he wasn’t even a client, just “an acquaintance, a casual friend met on a plane.” Although Waldron had never brought it up, that was when he decided that he wanted to become one of the firm’s clients.

“They were the only people who were able to answer my questions from a holistic standpoint,” he notes.

After leaving that job, Pendyala briefly joined an IT service firm run by an entrepreneur he had met through the Pittsburgh chapter of TIE (The Indus Entrepreneurs, a group started in the Silicon Valley, but now global of entrepreneurs from the Indus region, and dedicated to fostering entrepreneurship through primarily through education and mentoring). Within a short period, he realized that the world of IT was not for him. “It was all based on cost–whoever bids cheaper wins,” he explains. “The value-add was not very high.”

“I said this is not something I’m going to be very happy with,” he explains. “My passion has been coaching and mentoring so I decided to get professional training in being a professional life coach.”

In another one of the commonalities between him and John Waldron, at about the same time, Waldron had decided that he needed coaching and joined Strategic Coach in Chicago.

The two would compare notes on their progress every couple of months or so. One day Waldron asked Pendyala to join him in his office to sit-in on a class he had missed and was going to make-up over the phone. As part of the exercise Waldron had to make a list of the things he was exceptionally good at and another of things he didn’t care about at all.

After the session ended, Pendyala took a look at the two lists and told Waldron that what he needed was a COO. “At that time I was running my own firm, so I’m not the COO, I’m the entrepreneur,” Pendyala says. “That was the respect I had for COOs, all you need is a darn COO to take care of this crap. That’s what you need. Life will be easy for you. This is stuff you don’t care about, you don’t like but you need do in a business. And I think that clicked.”