Entrepreneur Twitter Drama Highlights the Price of Speaking Freely

Last month, entrepreneur Matt Mireles (pictured) published a tweet, asking: “Why is TechStars NYC run by a non-entrepreneur?”

The “non-entrepreneur” in question is 29-year-old David Tisch, whose grandfather built Loews into a Fortune 100 company that operates hotel chains, and whose family’s largess has helped bankroll numerous institutions, including the Tisch Galleries at the Metropolitan Museum of Art, and the Tisch School of the Arts at NYU. Since 2007, the young Tisch has been seed-funding startups with his brothers. According to his LinkedIn profile, he has also started two Internet companies, both of which were shuttered in less than a year’s time.

Surely, Mireles isn’t the first to wonder whether someone with Tisch’s background can fully appreciate the challenges that struggling entrepreneurs face. But the New York angel community’s reaction to Mireles’s apparently sincere question was surprisingly harsh. “I would recommend reserving judgment until you meet and know someone before you insult them publicly and passive-aggressively,” tweeted Chris Paik of Thrive Capital, a seed-fund in New York. Josh Stylman, an entrepreneur and seed investor who has stakes in Betaworks and GroupMe among other startups, called Mireles a “judgmental d**chebag” on Twitter.

Other comments were milder although somewhat defensive. “David is one of the good guys,” tweeted Hunch cofounder Chris Dixon, who is also a member of the seed-stage investment group Founder Collective. (Tisch smartly declined to weigh in, at least publicly.)

That something legitimate should cause so much consternation and trash-talking is concerning. Angel investors often claim that they provide an alternative to the rigid orthodoxy of venture investing. Collectively bashing an entrepreneur who dares to pose a reasonable question is more than unseemly: it’s as provincial as the herd mentality that many angels commonly associate with Silicon Valley VCs. No wonder Mireles fears his public smack-down could stifle other entrepreneurs from speaking openly about their opinions. As he told me yesterday, any entrepreneurs who “witnessed this little episode [will] be more afraid and less likely to call bullshit when they see it.”

Maybe Mireles doesn’t get much respect because his startup, SpeakerText, a transcription service for Web audio and video, isn’t setting the world on fire. SpeakerText recently raised more than $600,000, including from Lotus founder Mitch Kapor and Dave McClure’s 500 Hats, but it’s still eking out revenue by charging $2 per minute for the transcriptions. In fact, Mireles is still rooming with his cofounder.

Critics might also resent the attention Mireles has managed to attract through contrarian stances on his blog, The Metamorphosis. Indeed, a widely read post he wrote last year titled “Face It: New York is Not the Best Place for a Startup” couldn’t have endeared him to any of New York’s angel mafia. (Struggling in New York at the time, Mireles has since moved SpeakerText to San Francisco.)

While we chatted yesterday, I asked Mireles if the Bay Area has met the expectations he had before arriving. He called the benefits of Silicon Valley “double-edged. For someone like me, who’s a first-time entrepreneur and not particularly connected, there’s no better place to be.” For example, Netflix co-founder Marc Randolph is now an advisor. “That wouldn’t have happened if [we] weren’t living off [U.S. Highway] 101,” he said. “Most of my [entrepreneur] friends in New York don’t really have someone who they can call who has ‘been there, done that.’”

The downside, said Mireles, is “that if you stay here too long, there’s definitely a Silicon Valley groupthink.”

It’s no longer a West Coast problem alone. Mireles’s tweetfight was evidence of that — whether he realizes it or not.