StartUp Podcast: #18 Pitch Perfect 2
December 4, 2015 10:51 AM - Subscribe

Gimlet is growing fast. There are four shows on the air, and several others in pre-production. If they want to grow faster, though, they could use some more cash. Matt and Alex head back into the world of venture capital, deciding whether or not to raise another round of financing, this time, much bigger.
posted by radioamy (7 comments total)
Man, the flashback to first season StartUp Alex really hammered home how much he's changed. I forgot how tenative? Alex was about all decisions.
posted by selenized at 6:05 PM on December 4, 2015

$30 million!
posted by skewed at 8:07 AM on December 5, 2015

I don't know why Chris Sacca presses some button in me, but all his segments read to me as unrepentant asshole. Even while I understood and even agreed with what he was telling Alex. The new investor, Tim O'Shaughnessy, sounds much more like the kind of partner Gimlet could use.
posted by gladly at 8:44 AM on December 5, 2015

I like Chris Sacca's interview, he was a splash of cold water raising all sorts of questions that should have been asked and underlining how disconnected Alex seems to be from the money side of the business. Which is strange for a CEO, he should know in depth why they are pursuing key business decisions like raising more money.
posted by selenized at 10:43 AM on December 5, 2015 [1 favorite]

On the face of it, Graham Holdings (the new main investor) sounds ideal for Gimlet. But recall that LivingSocial - the company Tim O'Shaughnessy founded and ran for several years - is now the poster boy for overvalued billion dollar 'unicorn' startups, having lost around $1.4 billion from 2011-2014.
posted by adrianhon at 2:44 AM on December 6, 2015

Great episode! I liked the simple explanation of what raising a Series A is like. Although because Gimlet is in such a strong position with their product it went awfully easily for them. The usual process involves weeks of meetings, EIR visits to "research" your technology, unreturned calls, and no VC ever, ever saying "no". I'm glad Gimlet's had an easier time of it.

I know Chris Sacca, so I hear his appearances on this podcast differently. He's not an unrepentant asshole, he's a pretty decent guy. He's also blunt when appropriate. I think this episode edited him to sound blunt to highlight that splash of cold water thing. Blumberg wasn't prepared to talk to an investor about raising money; Sacca was making sure he understood that. It echoed the first season, with Sacca coaching Blumberg on how to give an elevator pitch.
posted by Nelson at 1:07 PM on December 31, 2015

It was funny how they wrapped up that section by saying "after I explained it to Sacca, he understood." I would have liked to hear that.
posted by smackfu at 5:45 PM on January 26, 2016

« Older Podcast: The Adventure Zone: E...   |  Movie: The Lion in Winter... Newer »

You are not logged in, either login or create an account to post comments