StartOut Live with Kara and Megan

The room was buzzing with anticipation - primarily because we didn't know if we were in for a lovefest or a bloodbath.  Kara Swisher, co-executive editor of The Wall Street Journal's All Things Digital, and famous for her eviscerating interviews of the technology world's movers and shakers, was about to grill Megan Smith, VP of New Business Development at Google and General Manager at Google.org.  But this time there was a twist in the interview dynamics.  Megan and Kara are spouses, live together, have two children together...was someone going to end up sleeping on the couch tonight?

The discussion was sponsored by StartOut, a new group created to help LGBT entrepreneurs learn the ropes of start up success from pioneers in the field.  Lorenzo Thione, one of StartOut's founders and the evening's emcee, is himself the creator of Bing!, Microsoft's search engine. 

The Swish didn't have to sleep on the couch after all.  Although she got some of her trademark wickedly funny barbs into the conversation - "Megan, you must have been such a supergeek in high school.  On the other hand, I was popular.  I wouldn't have even talked to you or acknowledged your existence" - this was clearly a conversation between two people who have great respect, love, and admiration for each other's talents and achievements. 

And the informality of the interview discussion format enabled Megan to share some of her thoughts and ideas about what makes technology entrepreneurship work - or not.  Some of her key insights during the discussion:

- Incrementalism is often a good thing.  Megan described how in the current start up climate, people are often looking for the next big paradigm-shifting idea.  But sometimes these ideas are TOO big - such that the infrastructure and user culture of the moment are not up to embracing and adopting these ideas.  For example, ideas like ipads and tablets and smart phones have been around for 30 years, but it is only now that we are culturally and technologically ready to consume these products on a mass market basis.  It took more incremental ideas like the Palm Pilot (which itself evolved incrementally from the concept that people wanted to be able to carry their contact lists around with them and modify them in a user friendly manner) to begin moving people step-by-step along the pathway that ultimately led to demand and desire for something like an iPhone.

- Right Idea, Wrong Platform.  Megan spent many years at the start up company General Magic, which Kara - reverting to the famous Swish "go-for-the-jugular" mode - understatedly described as "the most spectacular internet start up failure of its time."  Megan explained one of the key reasons that General Magic failed - that even though its founders were visionaries who 20 years ago were already conceptualizing cloud computing systems, they made key tactical errors.  In the cloud computing arena, they worked off of the concept of a closed system vs. an open source platform, which ultimately made the concept unworkable.  Megan's advice to budding entrepreneurs is to understand that lots of people have good ideas, but those ideas have to be rooted in strong engineering science and knowledge.  This is one of the reasons that Google insists that at least 50% of its workforce must at all times be composed of engineers.  And that every good idea must be developed in collaboration with an engineering corps which is highly attuned to all possible platform implementation options, new industry innovations, etc.

- Recognize Talent.  Megan's single biggest piece of advice for the audience is to recognize talent and leadership potential.  And to understand that the venture capital funders who finance many start up organizations are not necessarily the best people to identify either talent or leadership.  Particularly in the area of technology start ups, where the engineers often have a work ethic and culture that is vastly different from the financial services world with which most VC leaders are familiar, differences and mis-steps are common.  Megan underscored again the importance in entrepreneurial ventures of ensuring that business plans and models be driven from the core competence and talent of the product designers, and not to have leadership impose an artifical hierarchy from above.

And because it was Kara and Megan, the evening couldn't end without at least one zinger - this time directed at the make-up of the audience.  One attendee asked what is was like to be a woman in silicon valley, and Kara and Megan responded in unison, "Dudes!  It's all dudes!"  Added Kara, "It's all white, 30-something dudes.  Except Google, where the cafeteria at lunch time looks like the 'It's a Small World' ride at Disneyland.  But everywhere else, it's dudes.  Even at home.  We have two boys.  I tell you, we're surrounded by dudes."