Email First Startups

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

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

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.

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.

Facebook vs. Twitter: The Real-Time Battle

The power outage at Super Bowl 47 shined light on a growing issue for Facebook. Namely, its lack of relevancy during a live-event.

Super Bowl XLVII, the third most-watched program in television history, was accompanied by 52 national TV commercials, according to internet marketing site Marketing Land. Twitter was mentioned in 26 ads, or 50 percent, aired during CBS’ game coverage. Facebook took home four mentions for eight percent, while Google was not touted at all. YouTube and Instagram were both shown once.

Facebook and Twitter each received eight mentions out of a total of 59 national commercials during Super Bowl 46 in 2012, wrote Marketing Land. That means Twitter received more than two times as many mentions this year, while Facebook saw a 50 percent drop in big game ad mentions year-over-year.

(Read More: Twitter, Washington Post Also Announce Hacks )

Why are brands, who shelled out an average of $3.8 million per 30 second spot, shying away from a social network that has 1.06 billion users for a micro-blogging platform that has just 200 million users?

The first ever Posterous post

Almost six years ago, I started hacking on some Java code so I could email photos from my iPhone to my blog on Blogger. This is long before there was anything called “Posterous”.

I was just a photo blogger in New York, and I wanted to go mobile. So I started building, just for myself.

Here’s the very first post, running through the code that would later become Posterous At this point it was just me, working from my couch in NYC.


I hacked together a little code that lets me blog directly from my
iPhone, with pictures!

Stay tuned for more late night, drunk blogging. This could be a bad

via blog.isachin.com

What an incredible journey it has been. Over the past 5 years, I’ve worked with some of the best investors in the valley, collaborated with the best founders and startups in the world, and listened to and learned from an incredible set of users.

Most importantly, I get to work with the greatest team ever. It was all the hard work by the Posterous team that made the product loved by millions. Good times and bad, they stuck through it.

Thanks to everyone for the love and support. Especially my wife, Kate. It wasn’t easy dealing with the work hours, the late night pages, and the unreal amount of stress.

The team is thrilled to be a part of Twitter, and continuing on our mission here.

The @delta bait and switch tactic

Here’s Delta’s business model:

1. Sell you an inexpensive flight months in advance. Awesome. You book hotels, buy non refundable show tickets, make restaurant reservations, etc.

2. Closer to the flight date, Delta dramatically changes the details of the flight. Note: my latest change has me in *a different airport*. It’s NOT a small change.

3. They offer you a full refund, but at this point all the other airlines are more expensive since it’s so close to the flight date.

4. You have no choice but to keep the shitty Delta flight.

What I learned: go ahead and pay more up front to fly a better airline. It’s worth it.

Building Android first could make it harder to raise money

Last month a founder emailed me because he was looking to raise money for an app he’s building. He decided to build for Android first. I generally think that’s a smart move since Android growth is exploding, and there are fewer apps to compete with.

I sent this founder’s executive summary to some investors. The main response I got, “I don’t have an Android phone. Can you send me screenshots?”

I literally couldn’t get this person’s app in front of investors. I’m certain that this person will get less interest around his idea than if he had built the same app for iPhone.

This is just one example of the “Mobile Knowledge Gap Facing Investors” that Semil Shah blogged about:

for newer companies starting out that have significant mobile plans, founders may or may not be in a position to receive relevant guidance from their investors given how new and fast-moving mobile device adoption continues to grow.

Sure we all have iPhones. But that’s the problem: we all have iPhones. There’s no diversity in the Valley. Deep mobile knowledge is still rare. 

My advice:

If you decide to build for Android first, make sure you send investors screenshots, video tours, or any other material you can. Assume they don’t have an Android device. Or if they do, it’s not current.

It’s best to optimize for investors who will add value to your company beyond the cash they give you. Experience building a company, a strong network, and product advice are some things great investors can bring to the table.

Make sure that by choosing to build for Android first, you don’t close the door on some of the top investors available to you.

Our week in Japan

Japan is a country with the perfect balance of ancient culture and modern technology. Right next to a shrine that is hundreds of years old, you can get a Manhattan cocktail.

Japan imports nearly nothing. They have a sense of pride that says, “We can do it better.” And they do. Everything that exists in Japan is created with an attention to detail and a degree of perfection that I haven’t seen anywhere else.

Even our hotel bathroom was something to marvel at. The amazing washlet heated toilet seat (pretty much standard everywhere), fog free mirror, and super intuitive shower controls were incredible.

Even things that weren’t invented in Japan are made better there. It’s as if they sent their chefs to Paris, learned to make croissants from the best chefs in France, and then took it up a notch.

Oh the food. Wow. Sushi, ramen, tempura. And lots of French food. In Tokyo, the city with the most Michelin star restaurants, you will find no shortage of french food and french wine.

Tokyo is a city that rivals New York in my list of the top cities in the world. That’s a rank that I thought New York City held with a distant lead, but no longer.

Armed with a ton of great suggestions from our friends (thank you!), and our Lonely Planet guides, we set off to explore Japan.

Here’s how we did it (at least the major pieces):
Japan Rail
If there’s only one thing you do before leaving for Japan, it’s this: buy a Japan Rail pass. It gives you unlimited access to all Japan Rail trains. We used this to get between Tokyo and Kyoto, Tokyo and the airport, and a ton of local trains in both cities.
Day 1
  • Arrived in the evening
  • Staying at Hotel Marunouchi near Tokyo Station. Very nice and convenient
  • Cocktails at Bar Oak in the Tokyo Station Hotel. Gorgeous spot, killer drinks

Day 2

  • Tsukiji fish market
  • Ghibli museum (HIGHLY recommended)
  • Shibuya – ramen and shopping
  • Dinner and drinks with Sean (Twitter friend)

Day 3

  • Senso-ji temple
  • Asahi building – view and beer
  • Akihabara electronics district
  • Maid cafe (weird but fun)
  • Ginza for shopping
  • Ginza Lion beer hall
  • Four seasons for drinks with Tim, and foie (Apple friend)
  • L’atelier Roubechon for dinner, more foie

Day 4

  • Bullet train to Kyoto
  • Stayed at Hotel Granvia Kyoto. Ok, convenient.
  • Silver Pavilion
  • Lots of snacks along the way
  • Exploring Gion
  • Irish pub
  • Traditional tempura dinner – awesome!

Day 5

  • Hotel buffet
  • Gates of Shinto Shrine! Incredible.
  • Bamboo grove
  • Romantic beer by water 🙂
  • Golden temple
  • Gion for drinks

Day 6

  • Nishiki market
  • Train to Tokyo
  • Shinjinku
  • Drinks at Park Hyatt (nice but touristy)
  • French restaurant (Lugdunum Bouchon Lyonnais)
  • Karaoke for hours!

Day 7

  • Gyoza Ro for lunch
  • Harajuku craziness
  • Meiji Shrine
  • Roppongi: wine bar with 48 wines, self serve machines
  • Roppongi Hills for dinner

One of the best trips ever. I already miss Tokyo and want to go back.

You can see all our photos here.