throwaway724's comments

This also happened with a piece of shit OTC Facebook app developer called SNAP Interactive when Snapchat was going IPO. I met their CEO at a conference in NYC, and he literally had business cards printed out touting how high their market cap got during this and their subsequent message board pumping.

None of those things strike as 1) important or 2) indicative of a high-performing product development team given their size. But we can agree to disagree!

I really don't get it. Twitter has five thousand full-time employees. I have to assume at least 20% of them are in product development in some capacity. What exactly are these people doing all day? I can't point to a single notable product innovation they've had in years. And they continue to ignore the drumbeat of user asking for an edit button, and are completely unable to come up with any kind of reasonable solution to the abuse or bot problems.

I don't know Kayvon personally, but what exactly is wrong with Twitter that it's so bad and slow at product development? This should be #5000 on their list of things to do.

I really don't get it. Twitter has five thousand full-time employees. I have to assume at least 20% of them are in product development in some capacity. What exactly are these people doing all day?

I can't point to a single notable product innovation they've had in years. And they continue to ignore the drumbeat of user asking for an edit button, and are completely unable to come up with any kind of reasonable solution to the abuse or bot problems.

I don't know Kayvon personally, but what exactly is wrong with Twitter that it's so bad and slow at product development?

I'm increasingly of the opinion that technology like this will never see broad regulatory approval. I just can't see an argument where any agency will be comfortable with acceptable losses, and I don't see any endgame in which this technology does not result in an infinitesimal, but non-zero amount of fatal errors.

Sure. But in my experience, the amount in which investors posture that they're contrarian and look for unconventional opportunities versus how much they actually do is quite notably different.

Companies who raise $75mm don't lay off massive chunks of their workforce because they found product-market fit.

Justin raised $75mm because he's Justin, and for all VCs posture like they're contrarian risk-takers, they're absolutely not and would have invested in shit in a box if Justin said it was his.

Ehhhhhhhh. Auren ran one of the shadiest companies in recent history (Rapleaf) and he's discussing Thiel, who in my opinion was completely in the wrong w/r/t Gawker and is incredibly thin skinned and petty for someone who talks about the things that he does.

The core point is correct: you want (for lack of better phrasing) "out of the box" thinkers in your leadership roles, particularly in the early stages. But I would take either of those two as a model with the biggest grain of salt possible; you can be courageous and out of the box without being insanely unethical or a vampire-like dick, respectively.

Plenty of current athletes with lots of money to burn as well. I can count on one hand how many cases I've seen an athlete actually be value-add; in most cases they're the dumbest of dumb money who vastly overrate the influencer value of their social network.

Great, but how does that impact you? How are you going to edge companies who are much larger than you, for the finite number of skins allowed in each state? What's your plan for working with the regulators, including the necessary amount of lobbying and retail adjacency you need?

Just saying "Well, we can eventually become a paid host of these games" isn't enough and you haven't done that; just because it's now legal in a singular state doesn't mean that just anyone will be able to get licensed and regulated.

Posting anon due to industry reasons.

How in the world was this invested in?

1. It's unclear how, at least in the context of March Madness, this is preferable to any number of alternatives. Given that they don't touch money, it's functionally equivalent to either running an offline pool, or using an existing site with years upon years of consumer behavior and content integration like CBS, ESPN, or Yahoo!. Better UX? Yeah, maybe, but there are dozens of companies that have tried and failed on that premise in the fantasy space: FleaFlicker, Sleeperbot, and on and on. Some guy from the Apprentice had a company doing exactly this and spectacularly failed. People go where they already go as a habit, not to some new destination.

2. On the other formats, I'm skeptical that you'd have enough people willing to join pools around The Bachelor or what have you, or else you'd see it already. Even if I'm wrong, you run into the problem of (#3) plus generally a scale problem; that maxes around at a very low total unique visitor count.

3. Under the thesis that this might eventually turn into a platform that accepts and handles money, that seems extremely unlikely if you've seen how skin regulation has gone now that NJ is up and legalized. I can't see a world where an existing license holder would take a flyer on this when you've got the FanDuels and the DraftKings (not to mention the inevitable strong European entry in the market) with vastly larger budgets and user databases to leverage. Further to that, in the event these guys take off, there's absolutely no reason why those companies wouldn't just replicate this functionality. Anyone who follows Europe knows that over time, features diverge to parity.

It's going to be a dickish statement, but I don't see how it's not 100% true: there's no way this gets invested in if this kid's dad wasn't Joe Montana. Literally the only logic I could theoretically buy is that the name recognition of Joe Montana + YC would give them a shot at a license in a multi-skin state where a lower-end holder would be willing to give them a shot. Free to play either as a service (Chalkline, Sportcaller) or as the end game unto itself (#1, #2) is dead on arrival.

Hi everyone! Well, thank you for all of the comments - didn't expect my short little tale to be that interesting :)

As for me, it worked out - soon after arriving in NYC, I took a chance at starting a company for myself. Unlike Burbn/Instagram, which I would have liked from a market perspective, I went all-in on an idea and an industry that I truly loved. I managed to raise a little bit of funding, hired a great team, and exited 10x a few years later. Still at the company, now CTO. Love it more and more every day.

Right around the same time I started my company, I also met a beautiful woman who is now my wife. Bonus!

Do I think about what could have been? Sure. But I didn't let it stop me from plowing ahead and moving forward. What happened yesterday or last week or last year only impacts you to the extent that you let it. All you can ever do is believe in yourself and make the best decisions you can with the information available to you.

Posting anon.

In 2009, the startup where I was working was hitting the skids, and our investors (correctly) were not willing to back us. We all kept grinding for a month or two in honorable futility, but after a while, my bank account depleted and I had to go.

To make various ends meet and to keep my mental health during the wind down however, I took up some contract work that I found through various friends in the SF startup scene. One company that I really liked and did some small stuff for was Burbn, which was a mobile-only location check-in that was hinged around taking photos of your location.

Missing my friends in NYC (I made a lot of friends in SF, but my inner circle were my college buddies from CMU; I went to tech and they went finance, sigh), I decided to leave SF to head to NYC and get a fresh start.

As I was leaving, I wanted to tie up a few loose ends, so I emailed my contact at Burbn and said I was likely to be unavailable for any more work, but that I liked the project and hoped for the best for him. He responded and said that he was near funding on a small pivot, and that if I was interested, there might be a full-time role available. I declined - I was mentally done with SF and the startup scene (Larry Chiang, 111 Minna, the rise of FB spam-crap like RockYou, etc.) as it was then.

That person was Kevin Systrom; that pivot was Instagram.