On Startup Failure…

On Startup Failure…

A young entrepreneur (let’s call him “Turk”) approached me at an event recently, and he had an interesting dilemma. “I’m starting a new venture,” he said. “And I think it’s really good. But how do I make sure I’ve put together all the right pieces so I don’t fail?…”...
The Agony of “What Am I Supposed to Wear to an Investor Pitch?!”

The Agony of “What Am I Supposed to Wear to an Investor Pitch?!”

I was having lunch with a woman recently who I’ll call “Dior.” Dior has been a senior executive in a number of large media corporations and is now starting her own company and thinking about outside funding. We’d been having a lively conversation on different startup...
On the Importance of “I Don’t Think It Will Work…”

On the Importance of “I Don’t Think It Will Work…”

I was speaking to a founder who had gotten a meeting with a prominent VC recently.  Let’s call her “Red Shoes.” “Well, what did he say?” I asked. “He said he didn’t think it would work,” she said, clearly disappointed. “And?” “And what?” “And what else did he say?”...