My blog is now on WordPress. Why I chose this platform

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As all Posterous users look for new homes for their websites and blogs, I too needed to find a location for my thoughts and photos. This was my Posterous blog, and is now it’s on WordPress.com.

What was important to me when comparing options was:

  • A perfect migration process
  • A robust platform with the features I need, available today
  • Strong support for email, photos, and mobile
  • A platform with a strong community

After a bit of research, the decision was pretty clear. WordPress stood out as the winner among the pack. Many of the features that were so critical to me in the founding of Posterous, such as post by email, email subscriptions, comments, autopost, and magical url expansion, all exist on WordPress today.

Some of the things I’m loving:

  • The import process from Posterous is perfect. WordPress preserved my full size images, audio, video, text formatting, and other content.
  • Post by email works great. You can email a bunch of photos and get a beautiful gallery like the one in this post. It even pulls the exif data from photos. I don’t think I need Flickr anymore.
  • Strong commenting platform. Comment moderation, spam prevention through Akismet, and commenters can login using pretty much any method.
  • Analytics. I can see what traffic I’m getting on my site and other cool info, all built in. No need for Google Analytics.
  • Great themes. Definitely an area that Tumblr led for many years, but I found a bunch of themes on WordPress that I love. The engine is super flexible. I love the customizable sidebar.
  • Integrates with Twitter. Obviously very important to me. I love embedding tweets like this. You can embed anything by dropping a url in the post.
  • Subscribe by email. One of the most rare in my mind, but important. I want people (my family) to get an email when I post something. Who  actually visits blog sites or uses RSS? You can even reply to the email to leave a comment.
  • An API. Can’t emphasize how important this is. It’s a way for developers to build cool ways to get content on to your site (ie mobile apps) and also get your content out if you ever need to. Data portability is a must.
  • Great search. How can you be on the internet without search these days?
  • A ton of incredible documentation and a super strong worldwide community.
  • Cheap! For most users, it’s free. I’m paying just $13 per year because of my custom domain.

But most of all: the folks at WordPress are stellar people. They have an intense passion for what they do and the community they have built. They have been wonderful to work with over the past few months as we migrate Posterous users to their service.

Overall I’m really happy with the move. Blogging platforms have come a long way the past few years, and I’m confident WordPress will be pushing forward for years to come.

Email First Startups

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Last month, Ryan Hoover had a great post about building email into your startup first, before moving on to other platforms. His awesome points:

  • Email lets you validate ideas quickly
  • Since email is async, you can fake functionality with manual processes
  • Forces focus
  • Email is a part of users daily habits
  • Email is ubiquitous
  • You can use email to upsell users to other platforms when you’re ready

Posterous was the ultimate email first product. I started the project because I wanted to email photos from my iPhone to my blog. I wrote thousands of lines of email code, which posted to my Blogger blog, before I ever wrote a line of web code.

There are a few other reasons why I think email an amazing platform to build on top of:

  • Email has identity built in. Email is identity. Whether you’re sending or receiving email from users, you don’t need a login system. Posterous was able to completely eliminate signup from our flow.
  • Email is mobile. It’s on every device, including super low end feature phones. Even people in developing countries on slow internet connections can use email.
  • Email isn’t blocked in China. You open your service up to another billlion users.
  • Email is integrated in all the apps you use. You can email photos from iPhoto, or a link from Safari, or a Tweet from Twitter.
  • Email supports rich content. You can send photos, documents, video, audio, and any arbitrary attachment. There’s nothing email won’t transfer.
  • iPhones will send email in the background. If you’re sending a video and your internet is slow, the iPhone will keep uploading while Mail is in the background.
  • Users get notifications instantly, on all devices, without managing extra notification permissions or settings.
  • So easy, your mom can do it.

Email is a powerful and flexible platform used by billions of people around the world. Start your company with email first in mind, and integrate it deeply in everything you do.

Raising money from the best investors is more important than getting the highest valuation

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In the summer of 2008, Posterous was a part of Y Combinator Demo Day in Boston and Mountain View. After one of our demos, an investor pulled me aside:

“I love what you are doing. How much do you want? $3M? $5M?”

This was the Silicon Valley dream. An investor was throwing money at us.

But he wasn’t one of the top VCs, and this was my first company. I wanted strong advisors. So I politely declined, and instead raised an angel round from some of the best investors in the valley.

Vinod Khosla said it well:

Khosla explained that the key role of early investors is not funding, but personal attention and guidance. But generating buzz too early can inflate a startup’s market cap and make them a less lucrative investment of time and money for the top-tier advisors they need. That leads to critical missteps like poor hiring decisions that can doom a startup.

via techcrunch.com

Raising from the VC would have put more money in our bank account, and our valuation would have been astronomical. But it would have been worse for the company.

My advice: go into fundraising with a clear idea of how much money you want to raise. What is the next major milestone for the company and how much money do you need to hit that? Don’t over raise.

Then, optimize for the best investors in the valley. Find investors with a track record of success, check references, pick the one that’s the most passionate about what you’re doing.

The past couple years, I’ve seen many companies raise huge rounds at huge valuations. They got the money, but couldn’t scale their team or product effectively. Ultimately it became hard or impossible for them to raise another round, or find an exit.

Raising money isn’t success in and of itself. You have to be able to use that money to build real value within the company. Great investors and advisors will help you get there.

Play by your own rules – via Medium

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Play by your own rules.

Listen to your users more than the press. Don’t get sucked into the gravity hole between you and your competition. Ruthlessly run your own path, not someone else’s.

via medium.com

A great story about the Gowalla vs Foursquare battle. Can’t say I don’t see a ton of similiarities here with what happened with Posterous.

I started the company with an idea around mobile photo sharing using email. It was chasing the competition that took us down the route of blogging.

Blogging platforms already had a known feature set, a known set of success metrics, known competitors. It’s easier to enter an existing market as an underdog, than it is to do something truly new and unique.