Nate Westheimer

Business of Coding Interview by Nate Westheimer

When I first got started in tech, Gary Vaynerchuck was one of the first people to take me under his wing.

At the 2008 SXSW conference, Gary introduced me to many of the finest people in tech that I still know today, one of them being Joe Stump.

At the time, Joe was the Lead Architect of Digg, which in 2008 was one of the largest sites on the web. I remember thinking Joe was larger than life. A day after meeting him, I attended the Considerations of Scalable Web Ventures panel that Joe was on -- a panel which included other Internet Incredibles like Cal Henderson, Garret Camp, and Matt Mullenweg.

Though I didn't code yet, I was completely blown away what those guys did. I was especially blow away by Joe's ability to talk about scaling Digg in a way that even I understood, without dumbing it down.

By the end of that SXSWi, I was a Joe Stump fanboy.

Fast forward two and a half years later and Jackie and I found ourselves hitching a ride with Joe back to San Francisco, after attending Gary's Tahoe Tech Talks (we had stayed in touch and hung out since 2008).

During that ride, I told Joe that I was going to learn how to code when I got back from our West Coast trip. We talked for most of the ride from Tahoe to San Francisco about coding, but I'm pretty sure Joe still didn't believe me that I'd actually learn. I knew Joe had heard it all before, and I'm fairly sure I had said it all before.

Nevertheless, a week later, after we got back from San Francisco and armed with the advice of one of the smartest people I knew in the business, I sat down and really learned.

Fast forward three years again and it was my honor to sit down with Joe last summer (before I made the hop to CEO of Picturelife) and talk to him about life as a business-guy-turned-backend-lead. Today, his company Quick Left has posted our interview on their site.

I'm embedding the podcast below, but head to the Quick Left blog to check out the whole thing (and other posts they've done in their The Business of Coding series).

Twitter's Card Problem: The Photo Upload Anti-Pattern by Nate Westheimer

There is little doubt that "the card" will become a critical unit in the future of the World Wide Web.

App developers and marketers alike are climbing over each other to update their campaigns and websites to live in a "card" world, while startups like Wildcard are building out the much needed plumbing to help people take advantage of this new design pattern and extend it beyond Twitter's walls.

However, I see a major obstacle standing in the way of "card" adoption, and that's Twitter's separate, favored-nation treatment of photo uploads on their system.

Whereas Twitter only show users a small icon in their streams when a tweet contains a normal "card", Twitter prominently shows when a user (or a brand, or an app developer) uploads a photo. Here's an example from my Twitter stream this morning:

Photo uploads get favored over Twitter Cards

Photo uploads get favored over Twitter Cards

It is completely understandable why Twitter would want to favor user photos -- if your friend took and is sharing a photo, it's likely far more relevant than a visual summary of an article a friend is linking to. Screen space is in short supply, and so Twitter has to decide what to favor.

But, the problem is that this design decision is encouraging a nasty anti-pattern that threatens the future of cards and therefore threatens the future of a more usable, enjoyable Internet.

Because Twitter is so clearly favoriting directly uploaded photos over their own "photo card" format, app developers and publishers are skipping this new open standard and reverting back to direct uploads.

Take Business Insider, as an example. There is a very clear standard for marking up news articles with big images using Twitter Cards. It's appropriately called "Summary Card with Large Image."

However, being the clever company that Business Insider is, it chooses instead to upload the image used in the article, thereby greatly increasing the chances that its followers will actually see the post and click-through. And, while Twitter's photo upload API was clearly meant for users' real pictures, you can't blame Business Insider for "hacking" the use-case and getting more views.

Business Insider didn't use cards, it used a simple photo upload

Business Insider didn't use cards, it used a simple photo upload

While Business Insider may be one of the more aggressive publishers out there, high-growth, smart startups are also entering the fray, and in some cases are going back in Internet time, going from use of cards to cleverly generated images that look like cards.

Take our good friends at Timehop as an example. Last year they were an early adopter of Twitter's Cards standards, beautifully showing you a summary of your past moment right in your Twitter feed -- if you opened up the card.


Today, however, Timehop seems to have abandoned Twitter Cards, and has joined folks like Business Insider by simply doing a direct upload of their card as a rendered out image -- as if they were a user sharing a photo with friends.

As a user, fan and friend of Timehop (and a very tiny, indirect investor)*, I'm glad they've gone this new route to make sure I see more interesting Timehop content in my Twitter feed.

In fact, as soon as I saw what Timehop was doing I started building a prototype of how Picturelife could do the same thing, instead of using the aforementioned Twitter Photo cards. As with Business Insider, you definitely can't blame the publishers and developers for exploiting a design decision Twitter has made.

However, ultimately steering people away from open standards like "cards" is bad for the Internet and will attract as many bad actors as good actors using the system. It's like what happened with emails in the late 90s and early 2000s. Before best practices followed by Outlook and other popular email clients, web designers just started emailing full-text images of formatted text, eschewing HTML, machine readable text, and open standards for what "just worked."

Today, because email clients and spam filters have gotten better, and because search has become such an important part of email, this anti-pattern has reversed and sending an all-image email is left to the fake Viagra spammers of the world.

The good news is Twitter can get out in front of this quickly and reverse the trend.

The right thing for Twitter to do is not block the Business Insiders, Timehops, and Picturelife's of the world from using their media upload endpoint, it's to stop favoring media uploads over Twitter Cards in their interfaces.

My solution for Twitter would be rather simple: Twitter should invest in generating a quality score for all cards and direct uploads, and smartly obfuscate cards and photos from uploaders with low quality scores, and prominently display full cards and uploads from users, publishers, and developers with higher quality scores.

Twitter can reverse this anti-pattern if they act now. Until then, more of us will just start "hacking" Twitter and upload our cards as static photos.

Disclosure: Wildcard's CEO, Jordan Cooper, is a Partner at Lerer Ventures, an investor in Picturelife. Nate Westheimer is an investor in TechStars, which is an investor in Timehop.

On App Store Reviews by Nate Westheimer

Getting reviews in the App Store is so important that I'd love to add one of those spammy pop-ups to Picturelife's iOS app.

When you're fighting to succeed, it's understandable if you go for the most effective weapon, right?

Well, we think it's wrong and so we're not doing it.

Instead, we've come up with 7 ways to ask for App Store reviews that fit our idea of digital neighborliness.

I've posted about these ideas on Medium.

The Hard Thing... About Business Books by Nate Westheimer

It's 9:40pm on Monday night and I just put down Ben Horowitz's The Hard Thing About Hard Things.

I bought it at 4:45pm on Saturday, and the last time I read a book front-cover to back-cover like that was several years ago. It was that good.

It was so phenomenal, in fact, that I'm going to be buying a copy for each of my Red Bud CEOs and I'm going to encourage everyone on my team at Picturelife read it.

You don't have to be a CEO to get great information from this book.

But, for as much as I loved Ben's book and the rich, informative, and at times heart-breaking, stories it held, I could help but feel like it missed the mark for me in an important way every single business book seems to miss the mark for me: It wasn't written for me at all.

You see, at least fifty percent of The Hard Things... was only relevant to managing a company much larger, with much different issues than my startup, Picturelife.

Yes, we are a venture-backed, high-growth company (Spark is our lead investor and we have amazing angels like A16Z's own Chris Dixon), but most of Ben's book is centered on his Loudcloud story -- a company which raised $21m out of the gate, and $45m only 2 months after that.

Much of Ben's story was about managing a team of hundreds of people and several layers of bureaucracy within a couple of months of its founding. A company with less than 20 people is not the same.

For me, the hard thing about business books is how few of them actually speak to what I experience in the struggle (Ben's phrase). If it were just me, I wouldn't say anything about it and I would have stopped this post after my glowing review of The Hard Things..., but I think there are actually more venture-backed startups in my position than those in the LoudCloud position, and there aren't enough great stories told by the CEOs of those company who make it to the other side.

I don't want to take away anything from Ben's tremendous book -- it was immensely valuable to me as a new CEO, and ton's of the content was relevant to any manager or innovator -- however, I do want to make this call to the successful CEO community:

If any of you have a story that looks more like most of ours do, please share it. Who else has been 12 people a few years in and made it work?

I promise to write this story when Picturelife has made it to the other side, but in the meantime, who's going to step up to the plate. Who already has?