StartUp Podcast: Grow Big Or Go Home (Season 2 #2)
April 30, 2015 10:21 PM - Subscribe

We learn more about Dating Ring's experience in the highly competitive startup accelerator Y Combinator. Will they be in the 90% of YC companies that fail, or will they be the next Airbnb?

The intense three months bring all sorts of challenges and surprises for Lauren, Emma, and Katie. The pressure is on to grow as fast as possible, but a change in Facebook's advertising policy puts a snag in their customer acquisition strategy. They resort to making less-than-ideal matches, resulting in unhappy customers. An inquiry from a YC mentor encourages them to question their focus on "group dates," and the results from a customer survey causes them to pivot to focusing on one-on-one dates. Meanwhile, two of the founders question the amount of socializing the third is doing, leading to a blowout fight that never really gets resolved. The women try to recover in time to pitch 500 investors onstage at Demo Day. But is their app solid enough to grow Dating Ring into an actual business?

Plus, Alex reveals Gimlet's newest creation, Mystery Show with Starlee Kine.
posted by radioamy (12 comments total) 2 users marked this as a favorite
I haven't read ahead to see what happens with Dating Ring. But it strikes me as a poor fit for YC. If the whole model hinges on talented/skilled human matchmakers evaluating every user and picking dates for them, it's never going to scale to a massive size. They'll be limited by the number of matchmakers they can hire without compromising the quality of the matches. It's not like you can just outsource that to some call center (or if you can, it kind of undermines what they claim is their competitive advantage).

This isn't to say that it's can't be a great, profitable business. I think it can be. But I don't see how it can generate the kind of returns VCs expect without drastically changing their business model. And that's what I kind of hate about incubators. They can take businesses that can be really successful for their founders, and beloved by their users, and force them to pivot into a much narrower range of possibilities, just so that they can create outsized returns for their investors.
posted by primethyme at 8:31 AM on May 1, 2015

I agree, I don't really see how this business can scale. Then again, I'm not exactly sure how the business works because they haven't explained it that well. That may be intentional, however, since they're still talking about the early stages.

I thought this episode did a decent job of imparting on listeners the frenetic pace and stress of YC, but honestly I'm having a hard time getting into this season. The first season was compelling because you were hearing it first-person and much of the tape was recorded in real time. This is a lot of looking backwards and you're not hearing the panicky 3am confessionals or the actual founder equity conversations. I'm hoping that as the season moves forward we'll get some of that.
posted by radioamy at 10:47 AM on May 1, 2015

Paul Graham says Y Combinator encourages applicants to do things that don't scale, so they might be a better fit than first appears.
posted by smasuch at 12:43 PM on May 1, 2015 [2 favorites]

I agree that hearing them describe the fight (and of course, they didn't want to get into it too much, because who would) wasn't as arresting as hearing bits of it recorded would be. But I also appreciate that they're trying to figure out how this can work with a company that doesn't have editorial control over the podcast (and therefore is probably more worried about not embarrassing themselves). I'm interested in the story of DateRing and hope they keep the gas pedal on this season.
posted by Zephyrial at 3:47 PM on May 1, 2015 [1 favorite]

I'm having a harder time getting into this season as well. I think that part of it is that the world of Podcasting is more foreign to me than the world of tech companies going through YC (even though this one is unique in a number of ways). Listening to a public radio host pitch a podcasting company to Chris Sacca is far more interesting than listening to a 20-something founder pitch to YC execs. I'm pretty steeped in the startup scene, so it's something I already know a lot about, and don't necessarily need to hear more of. The fact that Dating Ring is not truly tech-oriented, and founded by three females without typical tech backgrounds, keeps it interesting to me. But so far it is nowhere near as compelling as the first season.

By the way, radioamy, I assume you're not the radioamy but every time I see your name I do a double take.
posted by primethyme at 9:35 PM on May 1, 2015

I've been enjoying more documentary-style podcasts lately and this seems to fit that bill pretty well. It's a pretty big departure from the first season and is maybe doing itself a little bit of a disservice by keeping the same name. They might have done well to give each season a subtitle, eg, Startup Season One: Gimlet Media so there's a cleaner break and better managed expectations.

The immediacy isn't there in the same way but I've still found myself pulling for Lauren and Emma. Though I would actually buy into some Bonus Content to get to know them better.

Also very excited for The Mystery Show.
posted by Tevin at 9:55 PM on May 1, 2015

This week feels more balanced than the previous ep, partly because the introductions are out of the way. It was a very competently done podcast that you could imagine being an ep of Planet Money.

However, I'm still struggling with the fact that a lot of the story - raising money, pitching to VCs, pivoting, etc. - is very familiar. No doubt part of that is on me, but I wonder how much that's the case with other listeners. In season 1, I felt like I was learning an awful lot, even though I know quite a bit about podcasting myself; I don't really feel like I'm learning much about VCs or dating this time.

Aside from that, I had one big problem. About two thirds of the way in, they mention Dating Ring was doing group dates at first, which was proving hard to scale. I did a genuine double-take when I heard that. Why didn't they mention that earlier? Everything we'd been told about Dating Ring up until that point was about matchmaking, and I had the impression that they'd always done one-on-one dating. I was irritated that this little bit of information was withheld until they could do a 'turns out' moment about pivoting.
posted by adrianhon at 9:23 AM on May 2, 2015 [3 favorites]

primethyme - ha, nope that's not me. By the time I got into twitter I had pretty much stopped using radioamy as a handle (and I was college radio not country radio).

adrianhon - I felt the exact same way about the group dates. I can't figure out why it felt so...devious.
posted by radioamy at 12:20 PM on May 2, 2015

Thirding the "Say wha'?" at the group dating thing - I mean, it was quite the twist in the tale! It did make me laugh, as I've been doing research into web UX, and the amount of times the creators of a site/service first do some user testing and discover that actual people respond very differently to what they expected is hilariously common.
posted by Gin and Broadband at 12:23 PM on May 4, 2015 [1 favorite]

I feel like they skipped over the part of the story that explains why this company is going the startup route, rather than the small company slow growth route. Like their competitive advantage is to have an experienced human matchmaker arrange dates, and they have exactly one matchmaker and under 500 clients. What would they do if 5000 people signed up?
posted by smackfu at 9:28 AM on May 7, 2015

(I now realize I repeated what the first couple of comments said. Oops!)
posted by smackfu at 9:28 AM on May 7, 2015

I'm looking forward to the Mystery Show.
posted by bq at 8:42 PM on May 14, 2015 [1 favorite]

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