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They say the Startup staff has interviewed a number of people, including Y Combinator partners and the head of competitor Match.

StartUp Podcast

Last year, Kay noticed a striking imbalance in the Dating Ring membership: In New York City, they had far more female clients, while their San Francisco database was dominated by men. So, the company cooked up a stunt: Cross-Country Love, a crowdfunded event where the company flew 16 single female New Yorkers out to the west coast for a long weekend of dates with Silicon Valley bachelors.

Not surprisingly, the trip got a lot of press —not all of it positive. No matter how successful a company ultimately becomes, you can be sure that its early days were peppered with missteps and failures—most minor, but a few likely painful and spectacular. So, why would anyone want to share those mistakes with the world?

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The company is the subject of season two of the podcast Startup , which premieres on Thursday. Startup devotes each season to chronicling the ups and downs of a single fledgling company. Listeners heard Blumberg stutter through disastrous VC pitches and agonize over whether he was taking the company in the right direction.

Stephan Labossiere Talks Dating Multiple People, Myths On Falling In Love + More

The tape caught dozens of fraught exchanges between Blumberg and his wife, his partner, his investors and several of his overworked employees. While almost every large media organization, including the New York Times, Atlantic , and BuzzFeed , has native advertising, it is not an ideal revenue stream.

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Also known as sponsored content or branded content, stories that companies pay for inherently blur the lines between editorial objectivity and advertising. Since Gimlet is not a nonprofit like NPR, it needs to play more ads during its shows to keep the lights on. Gimlet has succeeded in taking an otherwise annoying part of listening to a show, and turned it into an opportunity to do some great story telling while paying the bills.

Gimlet Media

It is also risky to depend largely on advertising. As Geektime has written about a lot in the past six months, the adtech sector has been going through a downturn and its bubble likely has already popped: Public investors like Fidelity have severely devalued adtech startups in their portfolio such as content recommendation engine Taboola , which they downgraded by half. Considering ad blockers have ruined the banner ad industry, one must also wonder when there will be ad blockers for all sorts of advertisements, including radio ads.

Hopefully Gimlet will have found other sources of revenue when that day comes.

She kindly spoke to us soon after the birth of her son Eliot: Meet Eliot, the youngest fan of podcaststartup. After receiving some media attention and participating in Y Combinator, arguably the most prestigious accelerator in Silicon Valley, the company was recommended to Chow as worthy of checking out.

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And for those out there wondering, the simple answer is yes, sex sells better than e-commerce even on the radio.