The opening title card of Butch Cassidy & The Sundance Kid reads, “Most of what follows is true.” The same could be said for the content of entrepreneur Jason Calacanis’s weekly video/audio podcast, This Week in Startups (or TWiST, as aggressively abbreviated throughout the show). Calacanis’s contract with his audience is that he will always speak his mind, and he will usually (but not always) be right.
Based on the episodes I’ve seen thus far, it’s hard to disagree. In this post-postmodern age of self promotion, where every individual is a self-branded social marketing expert (expert in the marketing of ME), a camera can be placed in front of anyone. The results are hit or miss. TWiST succeeds primarily through its honesty: it’s clear that every opinion and anecdote the host provides is passionate, unrehearsed, and (as promised) usually insightful. The show’s unvarnished production values lend to this authenticity — for a podcast that actually has sponsors and claims to run in the black, there’s a remarkably consistent lack of visible producing involved: transitions to phone callers, video and sound cues are nearly always muffed, and expletives are rarely edited out despite references to a human tape logger that exists solely for this purpose. Where this comes in most unwieldy is in each show’s running length: sessions can range from a little over an hour to just over two and a half hours. There’s something to admire in the sheer audacity of this fact, but on the whole one senses the same content could be delivered in half the time; sometimes less really is the same.
Episode 13 features many of the show’s recurring segments: there’s “Ask Jason,” reminiscent of the lightning round on Jim Cramer’s “Mad Money” where entrepreneurs call in to get Calacanis’s thoughts on their ideas; an interview with a featured entrepreneur (in this case Matt Mickiewicz, founder of SitePoint and 99designs); a segment called “The News,” where again Calacanis provides his off-the-cuff reactions to tech news stories; “The Deadpool,” where recently destructed startups are announced; and “Homework,” which appears to be an audio bookclub/marketing segment for Audible.com.
Calacanis’s personality and his ability to tell an engaging story are clearly the driving force behind the show — tangents are prone to superfluous name-dropping or backdoor bragging, but they’re usually more entertaining than not, ranging from a hilarious gift for hyperbole (“An iPhone costs what now, seventy thousand dollars a month?”) to comically vicious vendettas (pity Jimmy Wales, who had the poor misfortune to launch a competing product to Calacanis’s own Mahalo). Calacanis’s competitive East Coast personality is a surprisingly endearing love-hate proposition, though it’s hard to envision him occupying the same room as a Mark Cuban, one of his current investors. (For a good proxy, check out Episode 14 for some fascinating repartee between Calacanis and none other than Michael Arrington.)
Overall, the show could use the general tightening up that comes with practice. One hopes that Calacanis will eventually be able to quarterback the episodes to a more consistent length and content, both live and in the editing room. Guest interviews can probably follow a more standard template — perhaps prototypical of this space, Matt Mickiewicz proves an amiable but somewhat reticent fellow, requiring Calacanis to shoulder most of the work. The number of segments could also be cut or follow a rotating schedule.
Still, Calacanis’s heart is in the right place — his fierce desire to win, his belief in the middle class work ethic and his numerous marketing ploys to boost interest and traffic for himself and his sponsors — are all worthy of admiration. There’s also a generosity of spirit that can’t be faked; even in his harsher criticisms of pitches (during a new “Shark Tank” segment, where callers literally pitch their startup ideas to get feedback) it’s clear that he’s willing to stay open-minded and encouraging.
There’s no telling how long this train ride will last, but This Week in Startups would do well to stay true to its core passion and truths — it offers a fascinating viewpoint on the current zeitgeist of Silicon Valley entrepreneurs.