'Moneyball' Comes to Silicon Valley: What Technology Investor Dan Scheinman Sees

"Disruption" is so analog. Transformation is the word that will capture the new era of the mobile enterprise. Many legacy Fortune 500 tech giants -- Dell, Intel, Cisco, HP, Microsoft, Oracle, et al. -- are rushing to change as the static, analog PC Age they thrived in dies faster than anyone predicted.
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For all of the praise heaped on President Obama's technology advantage over Mitt Romney during his reelection campaign -- as told in the slide deck Inside the Cave: An In-Depth Look at the Digital, Technology, and Analytics Operations of Obama for America -- neither the debates nor mainstream media saw the impending storm that is about to change everything from how we share, interact, consume, collaborate and do business in the enterprise.

"Disruption" is so analog. Transformation is the word that will capture the new era of the mobile enterprise. Many legacy Fortune 500 tech giants -- Dell, Intel, Cisco, HP, Microsoft, Oracle, et al. -- are rushing to change as the static, analog PC Age they thrived in dies faster than anyone predicted.

What is taking place is a transformative power -- not disruption -- that isn't seen in generations, but over epochs of time. Three such thresholds of human innovation come to mind. The Phoenician alphabet (circa 1500 BCE), which became the foundation of Western language and eliminated the barrier to trade; the printing press (1440 CE) that spread copies of the written word; and oil and the automobile of the late 19th century, which propelled the average citizen to move out of city centers with suburban sprawl following their migration.

We are now entering the fourth epoch of human innovation: The Digital Age.

The digital umbrella encompasses cloud computing, mobility and big data analytics. Social media and metadata will play supporting roles in the tech transformation.

When Steve Jobs told President Obama at a Silicon Valley tech dinner that the overseas "jobs were never coming back" to America, the late CEO of Apple might as well have been referring to all those analog (paper), manual process, low-paying jobs that will be eliminated through automation, software and 3D printing.

From Analog to Digital

"We are moving from an analog world to an all digital one," Silicon Valley investor Dan Scheinman stated over a cup of tea in San Mateo, not far from where he grew up.

He sat forward, and said, "It amazed me that this push to digital was not discussed during the presidential debates. It will eliminate low value jobs for high value jobs. It was the single most important discussion in the presidential election and no one talked about it. We need to be at forefront of the digital change, not analog."

For all of the leverage that data analytics brought to the Obama Digital Campaign, including fundraising with well timed emails and push notifications to smartphones, which turned into mobile donations, the president who campaigned in 2008 on "change" discussed none of the real change that is heading our way.

The change will leave a trail of jobless people as long and scattered as the Titanic's debris field. Innovation has a way of altering the zeitgeist.

"Products in movies, music, and TV are going to change over the next five years," Mr. Scheinman said. "They will offer both enormous risk and opportunity in that space. Media, as a whole, is going to generate new opportunities."

Focus and Philosophy on Investment

"Venture capitalists of Silicon Valley won't invest in founders who are more than thirty-five years old. They don't do it. Knowing that, I look at being a contrarian -- an opportunist -- to find opportunities where the herd isn't," he said.

"A typical venture capital firm will look at 1,000 business plans each year. They will invest in fifteen of them. They are trained for pattern recognition. By reviewing so many (startups) they see common patterns on which type businesses should succeed," Mr. Scheinman said. "But there's a problem.

"I sat on a venture capital pitch before. Some entrepreneurs don't pitch well. But instead of engaging them, those in the room looked away. I realized I had to go to the source and ask questions. Go deep. Assume nothing. Look beyond the pattern for bigger returns," he answered. "Like in Moneyball, I look out of pattern. That includes founders who are more than thirty-five years old."

That would include this author, who is above that age. (Disclosure: Dan Scheinman is not investing in my startup Cloudnician).

"What do you look for in startups?" I asked.

"Big markets. Show success," he said. "But they can't get an audience with them (investors). They need to show success and execute, but they don't have inside access (to venture capital). Only five years ago, women were out of pattern. But now they are getting funded."

Digital in the Social Graph

"One of the seven investments I've made is in Tango. It's the intersection of mobile and social with 92 million users. It provides mobile-social networks of people on contact lists, relevant stuff, without the background noise of email," he said, finishing his tea. "It's the rise of mobile. It's a reaction against mass amount of data."

Dan Scheinman showed me the Tango app. It was a message from a venture capital friend, who shared a video tour of his house decorated for the holidays.

"So Tango works one to one," I noted.

"Yes. But soon it will be one to many," he said.

"Are there any big data startups you consider investing in?"

"There are two investments. A big analytics services company and data warehousing. The latter is the biggest change in datacenters to the cloud. It's the beginning of data to inform decisions. Investing heavily there and early," he said. "It's all moving west. All going digital."

Mr. Scheinman discussed his "amazing" baseball uniform collection, which covers the game from 1900 to 1951. As it became a hobby, he knew he needed to educate himself, since 10 percent of the uniforms in the market are fakes. So he hired a fabric specialist. In hindsight, had he known the prices were going to skyrocket, "I would have moved faster and bought more uniforms. They were so cheap then," he sighed with a grin.

It seems that the deep dive, methodical approach to learning more about an entrepreneur was honed in the sport he loves. "I became a reader of baseball history. The story lines stick with you. It's a noble pursuit. Finally, I have an answer for 'what is my hobby?'"

"How many boards do you sit on?"

"I sit on four boards," he said. "My role is as a strategist and an investor. I am a counselor for CEOs. I learned how to be a counselor, it's not about you, it's about them."

It appears that his years at Cisco -- he left in 2010 after two decades of M&A -- was also good for him, particularly the last few years, when he was SVP of Eos, a Cisco Media Solutions Group social entertainment platform. He reported directly to CEO John Chambers, and summed up the experience: "He's one of the few (Silicon Valley bosses) to work for. The company grew and to be a senior participant was special."

Although Eos shutdown -- it was technically good, but the "economics of entertainment was not great for us" -- he gained critical insight into what makes startup companies launch and succeed. Clearly, it's more than a great product. Positioning and brand carry as much weight for an emerging company to gain rapid adoption and scale.

"There are more changes hitting Silicon Valley than ever before. Ten years ago it was about selling tech to other businesses. Today, it's about creating new markets and disrupting businesses, more disruption and value than ever seen. Because of cloud, mobile, all going digital, the world is changing," he said. "But will be there enough jobs? The period we're in... it's 1929, the industrial physical economy is now moving to a digital economy."

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