Richard grew up in North San Diego where he worked on his parents’ tomato farm. Some of his earliest memories are of packing countless boxes all day on a Sunday. He also played little league, and when he went to college at Claremont McKenna College, he played on his college team. There he encountered a coach who taught him the art of pitching (that coach would later go on to manage the MLB’s San Diego Padres). 

Richard went into consulting after college and returned to it after business school at Northwestern (Kellogg) in Evanston, IL. In the mid-1990s, he wanted to transition into something more cutting edge, so he joined SGI, the company that invented CGI and whose big claim to fame was Jurassic Park. Richard had to take a pay cut to get into SGI, but it got him into high tech. But, it was about 18 months later that his career took an important turn, and Richard came back to Southern California.

A college friend introduced him to Goto.com, and he took another sizable pay cut to join as employee #35 in 1998. All he could afford at that point was a single room above a pawn shop on Colorado Blvd and bologna sandwiches for almost every meal. But, Goto was fun, because it was revolutionary. They were upsetting the economic model of the time, which accelerated the dot com crash at the end of the decade. They had this revolutionary idea that paid search was the future. The prevailing opinions at the time were that the “internet was free” and “paid search was icky.” That transition hastened the demise of a number of “dot bombs,” which I’m no longer bitter about at all. For the most part. 

On his first day at Goto.com, the company earned $5 in revenue. Yes, five. Not five “K” or five “MM.” Just five. Richard was its first Product Manager and ultimately oversaw their data systems and data analytics. His team tried to monetize the knowledge of where search customers came from and where they went. They were trying to work out a paid search deal with AOL, who controlled a lot of traffic at that point in history. 

A team of heavy hitters flew to San Francisco to meet with AOL, and Richard was brought along as the numbers guy, in case they got into specifics. As they arrived at the meeting, Richard volunteered to park the van while the rest of the team went in to start the meeting. When he finally got in, they’d already started talking specifics and numbers, so Richard jumped in and started rattling off cost per click, conversion rates and revenue projections. Within a few hours, they didn’t (yet) have a contract, but they had a deal, and paid search was coming to AOL. 

They only had one problem. Goto.com needed to buy the search space from AOL so that they could turn around and sell that to advertisers. That means that they needed a lot of money to prime this deal, and Goto was still operating on a startup budget. But, they did have one opportunity, thanks to Disney, who liked the Goto.com logo so much that they made a similar one for Go.com, a Disney property. Goto sued for trademark infringement, and eventually won $21.5M in the settlement. The timing was impeccable, and the amount was just right. Goto signed the check over to AOL, and paid search kicked off. Within a year, all the other major search providers signed up, too. If AOL was on board, then they assumed it was the future. Ha. That sounds pretty funny twenty years later. 

The next year, Yahoo bought Goto.com. That was the beginning of the end of Richard’s tenure there. He wearied of the trips to San Francisco to explain the same concepts over and over again. His team had been swimming in this data for years. They’d developed more than one billion-dollar idea in the field, and by this time the company was earning $6MM a day in revenues. They were experts in this new technology, and their new Yahoo overlords were just learning how to swing leg bones and sharpen rocks. Richard jumped at the chance to join another startup, Mezi Media, along with his same college friend.

Richard went from being poor and overworked to just being overworked. Mezi was brand new in the business of online comparison shopping and coupons. Richard worked from 7am to 8pm, took a break for dinner, and then worked from 9pm to 3am (stopping to feed his newborn son at 12am and 3am) managing the data team in China. Weeks like that turned into months, and Mezi Media climbed from nothing to top five in the industry within six months. When Valueclick (later Conversant) bought them, Richard was a two-year transition away from retirement, coaching baseball, joining the Pasadena Angels and volunteer board seats from La Canada to Claremont.

Since leaving Mezi Media, Richard has coached baseball for 11 years. Both of his boys played little league, and the youngest still has one more year, which equates to two more teams and two more opportunities to finish first. 

Richard has some very firm philosophies about baseball. The first is: listen to what the data is telling you. I guess that’s not a surprise, given who Richard is. You might think that’s unusual for a little league coach, and you’d be right. Richard tracks every pitch, not just whether it was a strike, but what kind of pitch it was, where it was, and what happened. That allows him to position his players to be able to make plays, and that gives them a sense of confidence. 

The really young kids have their coaches pitch to them. Richard described asking the kids to take a few practice swings and then pitching the ball in order to hit their bats. At first they’re surprised by the contact, and then you can see through their eyes as the belief catches fire in their minds that they can hit the ball. It’s that spark in the minds of children that keeps him spending hundreds of hours on a child’s game. 

Richard’s second tenet of baseball philosophy is to draft kids not for their size and skill but for their attitude. As a result, Richard’s teams almost always finish second in the standings, but I strongly suspect that they finish first in character formation and fun. He also keeps those two philosophies in mind when choosing startups to invest in.