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The Future Of Mentorship In An Age Of Entrepreneurs

If mentor-protege relationships have gone the way of the mainframe computer, where does that leave those of us who seek guidance?

Betting on People

Throughout my career as an investor, I have bet first and foremost on people. Ideas and products naturally may change and morph over time as they find their footing and markets – I rely on the founders I back to persevere through adversity, to stay true to their vision and to assemble world-class teams.

There's something happening here: entrepreneurship and the decline of corporate appeal

"There's somethin' happenin' here, what it is ain't exactly clear; 

Young people speaking their minds, gettin' so much resistance from behind..."

   - Buffalo Springfield

I am thoroughly enjoying spending the majority of my time with entrepreneurs.   I find that their enthusiasm, dedication, willingness to take huge risks and desire to make a dramatic impact quite inspiring.  This is especially true in light of the fact that the majority of start-ups fail.  While there are some statistics that say that entreprenuership overall is roughly holding steady (See, for example, Kauffman Foundation's Kauffman Index of Entrepreneurial Activity), inside the high technology arena it seems far different to me.

Retirement 2.0

Retirement 1.0:

When I left eBay in the summer of 2006, I had never not worked full time in my adult life. I had options available to me that I could only have imagined when I started my career: a wonderful wife and family who wanted more time with me, good career options (I sat on 5 boards at the time), and the economic freedom to do whatever I wanted with the rest of my life. However, I really struggled to get comfortable in this new situation. 

I remember clearly attending an event at our club and sitting next to a gentleman who told me that every day he would come to the club to eat breakfast, read his paper, hit the driving range, then play a round of golf. Good for him, but I told my wife I could never spend my time like that. I also struggled mightily with the concept of taking money from savings as opposed to putting money in. I knew economically that we were covered, but I was unprepared for the emotional struggle of not contributing.

But in less than six months of unemployment (and a few months from our youngest child heading off to college), I returned to work at the end of 2006 as CEO of LiveOps.

Playing Offense vs. Defense – New Management Practices for Work 2.0

“In the 21st century, if you’re looking for work, you shouldn’t have to search in the same old places and, once hired, you shouldn't have to clock in and clock out in the same old ways. We should be able to go beyond bricks and mortar and draw upon the information and communication technology of today.” 

– Newark, NJ Mayor Cory Booker   

State of the City Address, March 2, 2011  

Just like Newark Mayor Booker, I am rather bullish about where things are heading, and the opportunities in our grasp when we are proactive and look for new ways to solve the problems we face in our economy, education and jobs. For me, it is a switch from what I call defense mode to offense. Winning because we can and because we are willing to apply new ideas to create new opportunities and not just replacing what was lost.

Go Big or Go Home: It’s All About Doing Big Things

As anyone who knows me will tell you, I’m very passionate about what we do at LiveOps – not only because of the role we play in evolving the customer service industry, but because it creates an innovative and quality model for work. I couldn’t help but think about our work as I read the State of the Union address. A number of points struck a chord with me as a CEO but the one idea that resonated the most was:  ”We do big things.”

It reminds me of my time at eBay – we did so many big things – and this same spirit and opportunity is the reason I chose to join LiveOps.  We have been doing many big things.  But, amazingly, the most rewarding part is not in the “bigness,” but in the individual pieces that are ultimately responsible for building a powerful (and big) story.

In the Internet world we used to have a phrase – you probably know it (and you probably loathe it): Go Big or Go Home. Although I believe that anything worth doing is worth doing with every ounce of your being or not at all, that’s not what I’m talking about here.

The Next Killer App: Work

As a technologist, I'm obsessed with searching for the next killer app. Today, there are many companies that are offering amazing services and products that some may deem "killer apps." What I find interesting is that many of these are aimed at improving our virtual world--becoming a mayor on a social networking site, getting a hole in one or building an empire on a gaming site. It seems so simple when we escape for a few minutes (or hours) from our real world commitments to the fantastic online world we have created! But what about improving our offline "real" world?

Fireside Chat between Ron Conway and Maynard Webb

At the Webb Investment Network's first affiliate dinner, keynote speaker (and Silicon Valley legend) Ron Conway spoke with WIN founder Maynard Webb about trends in angel investing today, as well as advice for some of the affiliates newer to seed investing.

Innovation Beyond the Hype

Innovation has become an overused buzzword. That’s dangerous because people could tune it out and that would have big ramifications. All great change in the world comes from innovation; it is so vital to building a better future. We can’t afford for it to become overplayed and tired.

The Power of Giving Back: Nothing “Yeah, But” About It

I just returned from Aspen where I participated in Fortune Brainstorm: Tech, an annual gathering of tech leaders, media visionaries, entrepreneurs, and a variety of other big brained folks to talk about trends and changes in technology, culture and society as a whole.

The event, and particularly the public discussion I participated in about how technology can supercharge a new generation of nonprofits, left me newly inspired. It also further convinced me of the role giving back has in empowering businesses. As our nation grapples with how to maintain its leadership position in the global economy, we should view imbuing a spirit of philanthropy into our companies as one of the vital ways we can foster a culture of creativity, involvement, and commitment to doing good that will make not only individual companies, but our country as a whole stronger. (Companies that give back also gain the added benefit of attracting and retaining the right people.)

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